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{{chembox |
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| verifiedrevid = 390240985 |
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| Name = Pulvinone |
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| verifiedrevid = 445548490 |
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| ImageFile = (EZ)-Pulvinone Structural Formulae.png |
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| Name = Pulvinone |
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| imagename = mixture of ''cis''- and ''trans''-isomers |
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| ImageFile = Pulvinone Structural Formulae.svg |
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| ImageSize = 300px |
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| ImageName = mixture of ''cis''- and ''trans''-isomers |
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| IUPACName = (EZ)-5-Phenylmethylene-4-hydroxy-3-phenylfuran-2(5''H'')-one |
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| OtherNames = |
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| ImageSize = 300 |
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| ImageFileL1 = (E)-Pulvinone-3D-spacefill.png |
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| Section1 = {{Chembox Identifiers |
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| SMILES = |
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| ImageSizeL1 = 150 |
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| ImageAltL1 = Space-filling model of the (E)-pulvinone molecule |
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| CASNo = 4941-88-2 |
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| ImageCaptionL1 = (E)-pulvinone |
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| CASNo_Comment = (mixture of ''E''- and ''Z''-isomers) |
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| ImageFileR1 = (Z)-Pulvinone-3D-spacefill.png |
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| CASOther = 78376-10-0 (''Z''-isomer), 100074-80-4 (''E''-isomer) |
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| ImageSizeR1 = 150 |
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| ImageAltR1 = Space-filling model of the (Z)-pulvinone molecule |
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| ImageCaptionR1 = (Z)-pulvinone |
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| IUPACName = (''E''/''Z'')-5-Phenylmethylene-4-hydroxy-3-phenylfuran-2(5''H'')-one |
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| OtherNames = |
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|Section1={{Chembox Identifiers |
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| index1_label = (''Z'') |
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| index2_label = (''E'') |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = WRB2782R9H |
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| CASNo = 4941-88-2 |
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| CASNo_Comment = (''E''/''Z'') |
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| CASNo1_Ref = {{cascite|changed|??}} |
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| CASNo1 = 78376-10-0 |
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| CASNo2_Ref = {{cascite|changed|??}} |
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| CASNo2 = 100074-80-4 |
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| PubChem1 = 54678446 |
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| PubChem2 = 5358244 |
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| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} |
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| ChemSpiderID2 = 4513411 |
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| SMILES2 = c1ccc(cc1)/C=C/2\C(=O)C(=C(O2)O)c3ccccc3 |
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| InChI2 = 1/C17H12O3/c18-16-14(11-12-7-3-1-4-8-12)20-17(19)15(16)13-9-5-2-6-10-13/h1-11,19H/b14-11+ |
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| InChIKey2 = KDYDQZMQFZXGPJ-SDNWHVSQBO |
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| InChIKey = KDYDQZMQFZXGPJ-SDNWHVSQSA-N |
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| Section2 = {{Chembox Properties |
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|Section2={{Chembox Properties |
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| C=17 | H=12 | O=3 |
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| Formula = C<sub>17</sub>H<sub>12</sub>O<sub>3</sub> |
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| Appearance = Yellow needles |
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| MolarMass = 322,33 g/mol |
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| Density = |
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| Appearance = Yellow needles |
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| Solubility = Insoluble |
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| Density = ? g/cm<sup>3</sup>, ? |
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| MeltingPtC = 243 to 247 |
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| Solubility = |
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| MeltingPt_ref = <ref name="Ramage">{{cite journal | doi = 10.1039/P19840001539 | title = Dioxolanones as synthetic intermediates. Part 2. Synthesis of tetronic acids and pulvinones | year = 1984 | last1 = Ramage | first1 = Robert | last2 = Griffiths | first2 = Gareth J. | last3 = Shutt | first3 = Fiona E. | last4 = Sweeney | first4 = John N. A. | journal = Journal of the Chemical Society, Perkin Transactions 1 | pages = 1539}}</ref> |
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* Soluble in ], ] and ] |
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| BoilingPt = |
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* Insoluble in water |
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| MeltingPt = 243-247 °C <ref name="Ramage">R. Ramage, G. J. Griffiths, F. E. Shutt, J. N. A. Sweeney, ''J. Chem. Soc., Perkin Trans. 1'' '''1984''', 1539-1545 ].</ref> |
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| BoilingPt = |
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| Section3 = {{Chembox Structure |
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| Section7 = {{Chembox Hazards |
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|Section7={{Chembox Hazards |
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| ExternalSDS = |
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| ExternalMSDS = ] |
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| MainHazards = ] |
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| Section8 = {{Chembox Related |
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|Section8={{Chembox Related |
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| OtherFunction_label = |
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| Function = ] |
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| OtherFunctn = ] |
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| OtherCpds = ], ] |
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| OtherCompounds = ], ] |
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'''Pulvinone''', an ] belonging to the ]s, ]s, ]s and ]s classes, is a yellow crystalline ]. Although the pulvinone is not a ], several naturally occurring hydroxylated ]s are known. These hydroxylated pulvinones are produced by ] species, such as the in Europe common ] (''Boletus elegans'', also known as ''] grevillei''), or by ]s such as ''] Terreus''. |
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'''Pulvinone''', an ] belonging to the ]s, ]s, ]s and ]s classes, is a yellow crystalline ]. Although the pulvinone is not a ], several naturally occurring hydroxylated ]s are known. These hydroxylated pulvinones are produced by ] species, such as the in Europe common ] (''Boletus elegans'', also known as ''] grevillei''), or by ]s such as ''] terreus''. |
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==History== |
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==History== |
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] - such as ] -, ]s and ]s produce a wide range of pigments made up of one (]) or several (]) units of ]. In 1831, in the course of a study of the constituents of lichens (''Cetraria Vulpina''), the French chemist and pharmacist Antoine Bebert discovered a compound named ''vulpinic acid'', the first known naturally occurring methyl ester of pulvinic acid. More details about the structure of this pigment were disclosed in 1860 by the German chemists ] and ].<ref name="canstatt">''Canstatt's Jahresbericht über die Fortschritte in der Pharmacie und verwandte Wissenschaften in allen Ländern'', Harvard Universität, Jahrgang 10 (1861).</ref> While trying to elucidate the structure of vulpinic acid, the German chemist ] <ref name="Spiegel1">A. Spiegel, ''Ber. Dtsch. Chem. Ges.'' '''1880''', ''13'', 2, 1629-1635 ].</ref><ref name="Spiegel2">A. Spiegel, ''Ber. Dtsch. Chem. Ges.'' '''1880''', ''13'', 2, 2219-2221 ].</ref><ref name="Spiegel3">A. Spiegel, ''Ber. Dtsch. Chem. Ges.'' '''1881''', ''14'', 1, 873-874 ].</ref><ref name="Spiegel4">A. Spiegel, ''Ber. Dtsch. Chem. Ges.'' '''1881''', ''14'', 2, 1686-1696 ].</ref> found in 1880 that the ] could be ] to a diacid. He named the resulting diacid ]. The German chemist ]<ref name="Volhard">J. Volhard, ''Annal. Chem.'' '''1894''', ''282'', 1-21 ].</ref> elucidated the constitution of pulvinic acid by synthesizing it through the basic hydrolysis of a corresponding dicyanocompound. In the process, he also obtained small amounts of a side-product. One year later ] and Th. Ewan<ref name="Claisen_Ewan">L. Claisen, Th. Ewan, ''Annal. Chem.'', '''1895''', ''284'', 245-299 ].</ref> achieved the synthesis of this side-product and characterized it as the 5-benzylidene-4-hydroxy-3-phenylfuran-2(5H)-one. ] Claisen and Ewan described it as ''das der Pulvinsäure zu Grunde liegende Lacton'' (the lactone underlying the structure of pulvinic acid): that was the origin of the name pulvinone. |
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] (such as ]), ]s and ]s produce a wide range of pigments made up of one (]) or several (]) units of ]. In 1831, in the course of a study of the constituents of lichens (''Cetraria Vulpina''), the French chemist and pharmacist Antoine Bebert discovered a compound named ''vulpinic acid'', the first known naturally occurring methyl ester of pulvinic acid. More details about the structure of this pigment were disclosed in 1860 by the German chemists ] and ].<ref name="canstatt">''Canstatt's Jahresbericht über die Fortschritte in der Pharmacie und verwandte Wissenschaften in allen Ländern'', Harvard Universität, Jahrgang 10 (1861).</ref> While trying to elucidate the structure of vulpinic acid, the German chemist ]<ref name="Spiegel1">A. Spiegel, ''Ber. Dtsch. Chem. Ges.'' '''1880''', ''13'', 2, 1629-1635 {{doi|10.1002/cber.18800130293}}.</ref><ref name="Spiegel2">A. Spiegel, ''Ber. Dtsch. Chem. Ges.'' '''1880''', ''13'', 2, 2219-2221 {{doi|10.1002/cber.188001302237}}.</ref><ref name="Spiegel3">A. Spiegel, ''Ber. Dtsch. Chem. Ges.'' '''1881''', ''14'', 1, 873-874 {{doi|10.1002/cber.188101401183}}.</ref><ref name="Spiegel4">A. Spiegel, ''Ber. Dtsch. Chem. Ges.'' '''1881''', ''14'', 2, 1686-1696 {{doi|10.1002/cber.18810140230}}.</ref> found in 1880 that the ] could be ] to a diacid. He named the resulting diacid ]. The German chemist ]<ref name="Volhard">J. Volhard, ''Annal. Chem.'' '''1894''', ''282'', 1-21 {{doi|10.1002/jlac.18942820102}}.</ref> elucidated the constitution of pulvinic acid by synthesizing it through the basic hydrolysis of a corresponding dicyanocompound. In the process, he also obtained small amounts of a side-product. One year later ] and Thomas Ewan<ref name="Claisen_Ewan">L. Claisen, Th. Ewan, ''Annal. Chem.'', '''1895''', ''284'', 245-299 {{doi|10.1002/jlac.18952840302}}.</ref> achieved the synthesis of this side-product and characterized it as the 5-benzylidene-4-hydroxy-3-phenylfuran-2(5H)-one. ] Claisen and Ewan described it as ''das der Pulvinsäure zu Grunde liegende Lacton'' (the lactone underlying the structure of pulvinic acid): that was the origin of the name pulvinone. |
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==Natural occurrence== |
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==Natural occurrence== |
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Interestingly, it is only a century after the synthesis of the first pulvinone that the word ''Pulvinone'' turned into a collective term. In 1973, Edwards and Gill isolated the first naturally occurring hydroxylated pulvinone derivative.<ref name="Gill_Edwards">R. L. Edwards, M. Gill, ''J. Chem. Soc., Perkin Trans. 1'' '''1973''', 1921-1929. ].</ref> This trihydroxylated pulvinone was found as one of the main pigments responsible for the yellow colour of the stem and caps of the European mushroom ] (''Boletus elegans'', also known as '']''). |
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It was a century after the synthesis of the first pulvinone that the word ''pulvinone'' turned into a collective term. In 1973, Edwards and Gill isolated the first naturally occurring hydroxylated pulvinone derivative.<ref name="Gill_Edwards">R. L. Edwards, M. Gill, ''J. Chem. Soc., Perkin Trans. 1'' '''1973''', 1921-1929. {{doi|10.1039/P19730001921}}.</ref> This trihydroxylated pulvinone was found as one of the main pigments responsible for the yellow colour of the stem and caps of the European mushroom ] (''Boletus elegans'', also known as '']''). |
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In the very same year 1973, Seto and coworkers also found hydroxylated pulvinones in cultures of the ] ].<ref name="Seto1">N. Ojima, S. Takenaka, S. Seto, ''Phytochemistry (])'' '''1973''', ''12'', 2527-2529.</ref><ref name="Seto2">N. Ojima, K. Ogura, S. Seto, ''J. Chem. Soc., Chem. Commun.'' '''1975''', 717-718.</ref><ref name="Seto3">N. Ojima, S. Takenaka, S. Seto, ''Phytochemistry (])'' '''1975''', ''14'', 573-576.</ref> To insist on their origin - and thereby differentiate them from the hydroxylated pulvinones found in '']'' - Seto and coworkers named these compounds ''Aspulvinones''.<ref name="Seto4">N. Ojima, I. Takahashi, K. Ogura, S. Seto, ''Tetrahedron Lett.'' '''1976''', ''17'', 1013-1014.</ref><ref name="Seto5">I. Takahashi, N. Ojima, K. Ogura, S. Seto, ''Biochemistry'' '''1978''', ''17'', 2696-2702.</ref><ref name="Seto6">M. Kobayashi, N. Ojima, K. Ogura, S. Seto, ''Chem. Lett.'' '''1979''', 579-582.</ref><ref name="Seto7">H. Sugiyama, N. Ojima, M. Kobayashi, Y. Senda, J. Ishiyama, S. Seto, ''Agric. Biol. Chem.'' '''1979''', ''43'', 403-4.</ref> The ''aspulvinone'' terminology also incorporates a letter, indicating the order of chromatographic elution of these compounds (hence, the least polar aspulvinone was named Aspulvinone A, the one eluting next Aspulvinone B, etc...). |
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In the very same year 1973, Seto and coworkers also found hydroxylated pulvinones in cultures of the ] ].<ref name="Seto1">N. Ojima, S. Takenaka, S. Seto, ''Phytochemistry (])'' '''1973''', ''12'', 2527-2529.</ref><ref name="Seto2">N. Ojima, K. Ogura, S. Seto, ''J. Chem. Soc., Chem. Commun.'' '''1975''', 717-718.</ref><ref name="Seto3">N. Ojima, S. Takenaka, S. Seto, ''Phytochemistry (])'' '''1975''', ''14'', 573-576.</ref> To insist on their origin - and thereby differentiate them from the hydroxylated pulvinones found in '']'' - Seto and coworkers named these compounds ''Aspulvinones''.<ref name="Seto4">N. Ojima, I. Takahashi, K. Ogura, S. Seto, ''Tetrahedron Lett.'' '''1976''', ''17'', 1013-1014.</ref><ref name="Seto5">I. Takahashi, N. Ojima, K. Ogura, S. Seto, ''Biochemistry'' '''1978''', ''17'', 2696-2702.</ref><ref name="Seto6">M. Kobayashi, N. Ojima, K. Ogura, S. Seto, ''Chem. Lett.'' '''1979''', 579-582.</ref><ref name="Seto7">H. Sugiyama, N. Ojima, M. Kobayashi, Y. Senda, J. Ishiyama, S. Seto, ''Agric. Biol. Chem.'' '''1979''', ''43'', 403-4.</ref> The ''aspulvinone'' terminology also incorporates a letter, indicating the order of chromatographic elution of these compounds (hence, the least polar aspulvinone was named Aspulvinone A, the one eluting next Aspulvinone B, etc...). |
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Like many other yellow pigments in fungi and lichens, pulvinones can be traced back from the pulvinic acid pathway. The ''pulvinone'' structural unit is found in a number of natural products. All monomeric (such as ''pulvinic acid'' itself, ''vulpinic acid'', ''comphidic acid'', the ''aspulvinones'' and the ''Kodaistatins''<ref name="Kodaistatin">L. Vértesy, H.-J. Burger, J. Kenja, M. Knauf, H. Kogler, E. F. Paulus, N. V. S. Ramakrishna, K. H. S. Swamy, E. K. S. Vijayakumar, P. Hammann, ''J. Antibiot.'' '''2000''', ''53'', 677-686.</ref>) or oligomeric (''Badiones''<ref name="Steffan_Steglich">B. Steffan, W. Steglich, ''Angew. Chem., Int. Ed.'' '''1984''', 23, 6, 445-447. ].</ref>, ''Norbadione''<ref name="Gill_Lally">M. Gill, D. A. Lally, ''Phytochemistry'' '''1985''', ''24'', 1351-1354. ].</ref><ref name="LeGall_Mioskowski">T. Le Gall, C. Mioskowski, B. Amekraz ''et al.'' ''Angew. Chem., Int. Ed.'' '''2003''', 42, 11, 1289-1293. ].</ref>, ''Aurantricholon''<ref name="">D. Klostermeyer, L. Knops, T. Sindlinger, K. Polborn, W. Steglich ''Eur. J. Org. Chem.'' '''2000''', 4, 603-609. ].</ref>) derivatives of the pulvinic acid contain the ''pulvinone'' structural element. |
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Like many other yellow pigments in fungi and lichens, pulvinones can be traced back from the pulvinic acid pathway. The ''pulvinone'' structural unit is found in a number of natural products. All monomeric (such as ''pulvinic acid'' itself, ''vulpinic acid'', ''comphidic acid'', the ''aspulvinones'' and the ''Kodaistatins''<ref name="Kodaistatin">L. Vértesy, H.-J. Burger, J. Kenja, M. Knauf, H. Kogler, E. F. Paulus, N. V. S. Ramakrishna, K. H. S. Swamy, E. K. S. Vijayakumar, P. Hammann, ''J. Antibiot.'' '''2000''', ''53'', 677-686.</ref>) or oligomeric (''Badiones'',<ref name="Steffan_Steglich">B. Steffan, W. Steglich, ''Angew. Chem. Int. Ed.'' '''1984''', 23, 6, 445-447. {{doi|10.1002/anie.198404451}}.</ref> ''Norbadione'',<ref name="Gill_Lally">M. Gill, D. A. Lally, ''Phytochemistry'' '''1985''', ''24'', 1351-1354. {{doi|10.1016/S0031-9422(00)81131-0}}.</ref><ref name="LeGall_Mioskowski">T. Le Gall, C. Mioskowski, B. Amekraz ''et al.'' ''Angew. Chem. Int. Ed.'' '''2003''', 42, 11, 1289-1293. {{doi|10.1002/anie.198404451}}.</ref> ''Aurantricholon''<ref>D. Klostermeyer, L. Knops, T. Sindlinger, K. Polborn, W. Steglich ''Eur. J. Org. Chem.'' '''2000''', 4, 603-609. {{doi|10.1002/anie.200390332}}.</ref>) derivatives of the pulvinic acid contain the ''pulvinone'' structural element. |
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So far, all naturally occurring pulvinone derivatives were found to be ''Z''-configured. |
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So far, all naturally occurring pulvinone derivatives were found to be ''Z''-configured. |
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==Pharmacological properties== |
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==Pharmacological properties== |
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* Rehse ''et al.''<ref name="Rehse1">K. Rehse, J. Wagenknecht, N. Rietbrock, ''Arch. Pharm. (Weinheim, Ger.)'' '''1978''', ''311'', 986-991.</ref><ref name="Rehse2">K. Rehse, U. Emisch, ''Arch. Pharm. (Weinheim, Ger.)'' '''1982''', ''315'', 1020-1025.</ref><ref name="Rehse3">K. Rehse, J. Schinke, G. Bochert, ''Arch. Pharm. (Weinheim, Ger.)'' '''1979''', ''312'', 390-394.</ref><ref name="Rehse4">K. Rehse, J. Lehmke, ''Arch. Pharm. (Weinheim, Ger.)'' '''1985''', ''318'', 11-14.</ref> showed the anti-coagulant activity of some pulvinones in rats. |
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* Rehse ''et al.''<ref name="Rehse1">K. Rehse, J. Wagenknecht, N. Rietbrock, ''Arch. Pharm. (Weinheim, Ger.)'' '''1978''', ''311'', 986-991.</ref><ref name="Rehse2">K. Rehse, U. Emisch, ''Arch. Pharm. (Weinheim, Ger.)'' '''1982''', ''315'', 1020-1025.</ref><ref name="Rehse3">K. Rehse, J. Schinke, G. Bochert, ''Arch. Pharm. (Weinheim, Ger.)'' '''1979''', ''312'', 390-394.</ref><ref name="Rehse4">K. Rehse, J. Lehmke, ''Arch. Pharm. (Weinheim, Ger.)'' '''1985''', ''318'', 11-14.</ref> showed the anti-coagulant activity of some pulvinones in rats. |
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* At the beginning of the 80s, the companies ] and ] patented a large number of derivatives of the vulpinic acid because of their anti-inflammatory, anti-fever and pain-killing properties. Yet vulpinic acid - as well as many of its derivatives - is a ] compound. Since pulvinones exhibit a lower cytotoxicity compared to vlupinic acid and its derivatives, ] investigated the pharmaceutical potential of more than 100 pulvinones <ref name="Campbell">A. C. Campbell, M. S. Maidment, J. H. Pick, D. F. M. Stevenson, ''J. Chem. Soc., Perkin Trans. 1'' '''1985''', 1567-1576. ].</ref>. To date, the results of these studies were not fully disclosed. |
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* At the beginning of the 80s, the companies ] and ] patented a large number of derivatives of the vulpinic acid because of their anti-inflammatory, anti-fever and pain-killing properties. Yet vulpinic acid - as well as many of its derivatives - is a ] compound. Since pulvinones exhibit a lower cytotoxicity compared to vulpinic acid and its derivatives, ] investigated the pharmaceutical potential of more than 100 pulvinones.<ref name="Campbell">A. C. Campbell, M. S. Maidment, J. H. Pick, D. F. M. Stevenson, ''J. Chem. Soc., Perkin Trans. 1'' '''1985''', 1567-1576. {{doi|10.1039/P19850001567}}.</ref> To date, the results of these studies were not fully disclosed. |
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* In 2005, the ] company patented biphenyl-substituted pulvinones<ref name="Caufield">C. E. Caufield, S. A. Antane, K. M. Morris, S. M. Naughton, D. A. Quagliato, P. M. Andrae, A. Enos, J. F. Chiarello, J. (Wyeth, and Brother Ltd., USA), ''WO 2005019196'', ''US 2005054721'', '''2005'''.</ref><ref name="Antane">S. A. Antane, C. E. Caufield, W. Hu, D. Keeney, P. Labthavikul, K. M. Morris, S. M. Naughton, P. J. Petersen, B. A. Rasmussen, G. Singh, Y. Yang, ''Bioorg. Med. Chem. Lett.'' '''2006''', 176-180. ].</ref> due to their promising activity against Gram-positive bacteria, including otherwise ]. However, pulvinone-based antibiotics were so far only patented for animal use. |
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* In 2005, the ] company patented biphenyl-substituted pulvinones<ref name="Caufield">C. E. Caufield, S. A. Antane, K. M. Morris, S. M. Naughton, D. A. Quagliato, P. M. Andrae, A. Enos, J. F. Chiarello, J. (Wyeth, and Brother Ltd., USA), ''WO 2005019196'', ''US 2005054721'', '''2005'''.</ref><ref name="Antane">S. A. Antane, C. E. Caufield, W. Hu, D. Keeney, P. Labthavikul, K. M. Morris, S. M. Naughton, P. J. Petersen, B. A. Rasmussen, G. Singh, Y. Yang, ''Bioorg. Med. Chem. Lett.'' '''2006''', 176-180. {{doi|10.1016/j.bmcl.2005.09.021}}.</ref> due to their promising activity against Gram-positive bacteria, including otherwise ]. However, pulvinone-based antibiotics were so far only patented for animal use. |
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==Chemical properties== |
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==Chemical properties== |
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Pulvinone is a ], more precisely an ] ester of the ''trans-1,4-diphenyl-2,3-dihydroxy-1,3-butadiene-1-carboxylic acid'', from which it can be prepared through removal of one ] of water: |
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Pulvinone is a ], more precisely an ] ester of the ''trans-1,4-diphenyl-2,3-dihydroxy-1,3-butadiene-1-carboxylic acid'', from which it can be prepared through removal of one ] of water:{{cn|date=January 2022}} |
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The central 5-membered ring core of pulvinone reveals a 4-hydroxy-] structure. They are essentially found in their ] form, which exhibits acidic properties due to the relative lability of the hydroxylic proton. 4-hydroxy-]s such as pulvinones are therefore referred to as ]s, and belong to the larger category of ] acids. |
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The central 5-membered ring core of pulvinone reveals a 4-hydroxy-] structure. They are essentially found in their ] form, which exhibits acidic properties due to the relative lability of the hydroxylic proton. 4-hydroxy-]s such as pulvinones are therefore referred to as ]s, and belong to the larger category of ] acids. |
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==Biosynthesis== |
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==Biosynthesis== |
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The fungal biosynthesis starts from aromatic aminoacids such as ] and ]; after oxydeamination to the corresponding arylpyruvic acid, the pulvinone skeleton is formed by a sequence of dimerisation, oxidative ring-cleavage and decarboxylation.<ref name="Gill_Steglich">M. Gill, W. Steglich, ''Prog. Chem. Org. Nat. Prod.'', '''1987''', ''51'', 1-317. ].</ref> |
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The fungal biosynthesis starts from aromatic aminoacids such as ] and ]; after oxydeamination to the corresponding arylpyruvic acid, the pulvinone skeleton is formed by a sequence of dimerisation, oxidative ring-cleavage and decarboxylation.<ref name="Gill_Steglich">{{cite book | author = Gill, M. & Steglich, W. | chapter = Pigments of Fungi (Macromycetes) | date = 1987 | title = Fortschritte der Chemie organischer Naturstoffe / Progress in the Chemistry of Organic Natural Products | journal = Fortschritte der Chemie Organischer Naturstoffe = Progress in the Chemistry of Organic Natural Products. Progres dans la Chimie des Substances Organiques Naturelles | volume = 51 | pages = 1–297 | pmid = 3315906 | doi = 10.1007/978-3-7091-6971-1_1 | isbn = 978-3-7091-7456-2 }}{{Page range too broad|date=January 2020}}</ref>{{Page range too broad|date=January 2020}} |
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], Pulvinic acids and Pulvinones.<ref name="Gill_Steglich"/>{{Page range too broad|date=January 2020}}]] |
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==Total synthesis== |
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==Total synthesis== |
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] was the first to synthesise vulpinic acid, pulvinic acid and pulvinone<ref name="Volhard"/>. |
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] was the first to synthesise vulpinic acid, pulvinic acid and pulvinone.<ref name="Volhard"/> |
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To date, 11 ] of pulvinones were reported: |
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To date, 11 ] of pulvinones were reported: |
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* 1895 by Claisen and Ewan<ref name="Claisen_Ewan"/>, |
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* 1895 by Claisen and Ewan,<ref name="Claisen_Ewan"/> |
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* 1975 and 1979 by Knight and Pattenden<ref name="Knight_Pattenden1">D. W. Knight, G. Pattenden, ''J. Chem. Soc., Chem. Commun.'' '''1975''', 876-877 ].</ref>,<ref name="Knight_Pattenden2">D. W. Knight, G. Pattenden, ''J. Chem. Soc., Perkin Trans. 1'' '''1979''', 70-76 ].</ref>, |
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* 1975 and 1979 by Knight and Pattenden,<ref name="Knight_Pattenden1">D. W. Knight, G. Pattenden, ''J. Chem. Soc., Chem. Commun.'' '''1975''', 876-877 {{doi|10.1039/C39750000876}}.</ref><ref name="Knight_Pattenden2">D. W. Knight, G. Pattenden, ''J. Chem. Soc., Perkin Trans. 1'' '''1979''', 70-76 {{doi|10.1039/P19790000070}}.</ref> |
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* 1979 by Jerris, Wovkulich and Amos B. Smith III<ref name="Smith">P. J. Jerris, P. M. Wovkulich, A. B. Smith III, ''Tetrahedron Lett.'' '''1979''', 20, 4517-20 ].</ref>, |
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* 1979 by Jerris, Wovkulich and Amos B. Smith III,<ref name="Smith">P. J. Jerris, P. M. Wovkulich, A. B. Smith III, ''Tetrahedron Lett.'' '''1979''', 20, 4517-20 {{doi|10.1016/S0040-4039(01)86637-5}}.</ref> |
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* 1984 by Ramage ''et al.''<ref name="Ramage"/>, |
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* 1984 by Ramage ''et al.'',<ref name="Ramage"/> |
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* 1985 by Campbell ''et al.''<ref name="Campbell"/>, |
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* 1985 by Campbell ''et al.'',<ref name="Campbell"/> |
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* 1990 by Gill ''et al.''<ref name="Gill2">M. Gill, M. J. Kiefel, D. A. Lally, A. Ten, ''Aust. J. Chem.'' '''1990''', ''43'', 1497-518.</ref>, |
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* 1990 by Gill ''et al.'',<ref name="Gill2">M. Gill, M. J. Kiefel, D. A. Lally, A. Ten, ''Aust. J. Chem.'' '''1990''', ''43'', 1497-518.</ref> |
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* 1991 by Pattenden, Turvill and Chorlton<ref name="Pattenden">G. Pattenden, M. W. Turvill, A. P. Chorlton, ''J. Chem. Soc., Perkin Trans. 1'' '''1991''', ''10'', 2357-2361. |
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* 1991 by Pattenden, Turvill and Chorlton,<ref name="Pattenden">G. Pattenden, M. W. Turvill, A. P. Chorlton, ''J. Chem. Soc., Perkin Trans. 1'' '''1991''', ''10'', 2357-2361. |
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].</ref>, |
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{{doi|10.1039/P19910002357}}.</ref> |
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* 2005 by Caufield ''et al.''<ref name="Caufield"/>, |
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* 2005 by Caufield ''et al.'',<ref name="Caufield"/> |
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* 2006 by Antane ''et al.''<ref name="Antane"/>, |
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* 2006 by Antane ''et al.'',<ref name="Antane"/> |
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* 2007 by Kaczybura and Brückner<ref name="Brückner1">N. Kaczybura, R. Brückner ''Synthesis'' '''2007''', 118-130. ].</ref>, |
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* 2007 by Kaczybura and Brückner,<ref name="Brückner1">N. Kaczybura, R. Brückner ''Synthesis'' '''2007''', 118-130. {{doi|10.1055/s-2006-950378}}.</ref> |
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* 2007 by Bernier, Moser and Brückner<ref name="Brückner2">D. Bernier, F. Moser, R. Brückner ''Synthesis'' '''2007''', 15, 2240-2248. ].</ref><ref name="Brückner3">D. Bernier, R. Brückner ''Synthesis'' '''2007''', 15, 2249-2272. ].</ref>. |
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* 2007 by Bernier, Moser and Brückner.<ref name="Brückner2">D. Bernier, F. Moser, R. Brückner ''Synthesis'' '''2007''', 15, 2240-2248. {{doi|10.1055/s-2007-983800}}.</ref><ref name="Brückner3">D. Bernier, R. Brückner ''Synthesis'' '''2007''', 15, 2249-2272. {{doi|10.1055/s-2007-983803}}.</ref> |
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==Sources== |
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== See also == |
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== Sources == |
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