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{{Chembox |
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{{Chembox |
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| Watchedfields = changed |
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| verifiedrevid = 445851533 |
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| verifiedrevid = 447244733 |
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| ImageFile = Magellanine.svg |
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| ImageFile = Magellanine.svg |
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| ImageSize = 200px |
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| ImageSize = |
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| IUPACName = (4a''S'',6''S'',6a''R'',6b''S'',10a''S'',11a''S'')-6-Hydroxy-3,9-dimethyl-4,4a,5,6,6a,6b,7,8,9,10,10a,11-dodecahydro-1H-benzopentalenopyridin-1-one |
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| PIN = (4a''S'',6''S'',6a''R'',6b''S'',10a''S'',11a''S'')-6-Hydroxy-3,9-dimethyl-4,4a,5,6,6a,6b,7,8,9,10,10a,11-dodecahydro-1''H''-benzopentalenopyridin-1-one |
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| OtherNames = |
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| OtherNames = |
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| Section1 = {{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| CASNo = 61273-75-4 |
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| CASNo = 61273-75-4 |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| PubChem = 442489 |
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| UNII = BLX5LW8WRA |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| PubChem = 442489 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 390919 |
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| ChemSpiderID = 390919 |
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| SMILES = O=C1/C=C(/C)C214((O)C2)3(CN(C)CC3)C4 |
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| SMILES = O=C1/C=C(/C)C214((O)C2)3(CN(C)CC3)C4 |
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| InChI = 1/C17H25NO2/c1-10-5-12-7-14(19)16-13-3-4-18(2)9-11(13)8-17(12,16)15(20)6-10/h6,11-14,16,19H,3-5,7-9H2,1-2H3/t11-,12+,13+,14+,16+,17-/m1/s1 |
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| InChI = 1/C17H25NO2/c1-10-5-12-7-14(19)16-13-3-4-18(2)9-11(13)8-17(12,16)15(20)6-10/h6,11-14,16,19H,3-5,7-9H2,1-2H3/t11-,12+,13+,14+,16+,17-/m1/s1 |
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| InChIKey = ADRPSBGLUHNVOU-INSRFAMQBF |
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| InChIKey = ADRPSBGLUHNVOU-INSRFAMQBF |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 1S/C17H25NO2/c1-10-5-12-7-14(19)16-13-3-4-18(2)9-11(13)8-17(12,16)15(20)6-10/h6,11-14,16,19H,3-5,7-9H2,1-2H3/t11-,12+,13+,14+,16+,17-/m1/s1 |
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| StdInChI = 1S/C17H25NO2/c1-10-5-12-7-14(19)16-13-3-4-18(2)9-11(13)8-17(12,16)15(20)6-10/h6,11-14,16,19H,3-5,7-9H2,1-2H3/t11-,12+,13+,14+,16+,17-/m1/s1 |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = ADRPSBGLUHNVOU-INSRFAMQSA-N |
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| StdInChIKey = ADRPSBGLUHNVOU-INSRFAMQSA-N |
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}} |
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| Section2 = {{Chembox Properties |
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|Section2={{Chembox Properties |
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| C=17|H=25|N=1|O=2 |
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| C=17 | H=25 | N=1 | O=2 |
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| Appearance = |
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| Appearance = |
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| Density = |
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| Density = |
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| MeltingPt = 165-166 °C<ref name=Castillo/> |
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| MeltingPtC = 165 to 166 |
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| MeltingPt_ref = <ref name=Castillo/> |
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| BoilingPt = |
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| Solubility = |
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| BoilingPt = |
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| Solubility = |
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}} |
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| Section3 = {{Chembox Hazards |
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| MainHazards = |
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| FlashPt = |
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| Autoignition = |
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|Section3={{Chembox Hazards |
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| MainHazards = |
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| FlashPt = |
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| AutoignitionPt = |
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}} |
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'''(-)-Magellanine''' is a member of the '']'' ] class of natural products. It was isolated from the club moss '']'' in 1976.<ref name=Castillo>, 1976, 54:(18) 2893-2899. </ref> It has been synthesized five times, with the first ] having been completed by the ] group at the ] in 1993.<ref>J. Am. Chem. Soc., 1993, 115 (7), pp 2992–2993. </ref> It has also been synthesized by the ] group in 1993 at ],<ref>J. Am. Chem. Soc., 1994, 116 (11), pp 4689–4696. </ref> the Chun-Chen Liao group in 2002 at ],<ref>Angew. Chem. Int. Ed. 2002, 41, No. 21, 4090-4093. </ref> the Miyuki Ishikazi and Tamiko Takahashi groups in 2005 at the ] and ],<ref>Tetrahedron 61 (2005) 4053–4065. </ref> and the Chisato Mukai group in 2007 at the ].<ref>J. Org. Chem. 2007, 26, 10147-10154.</ref> One partial synthesis was completed by the A. I. Meyers group in 1995 at ]. <ref>, Chem. Commun., 1995, 2511-2512. </ref> |
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'''(−)-Magellanine''' is a member of the '']'' ] class of natural products. It was isolated from the club moss '']'' in 1976.<ref name=Castillo>{{cite journal | year = 1976 | title = Isolation and Structure | journal = Canadian Journal of Chemistry | volume = 54 | issue = 18| pages = 2893–2899 | doi=10.1139/v76-409 | last1 = Castillo | first1 = Mariano | last2 = Loyola | first2 = Luis A. | last3 = Morales | first3 = Glauco | last4 = Singh | first4 = Ishwar | last5 = Calvo | first5 = Crispin | last6 = Rolland | first6 = Herbert L. | last7 = MacLean | first7 = David B.| doi-access = free }}</ref> It has been synthesized five times, with the first ] having been completed by the ] group at the ] in 1993.<ref>{{cite journal|doi=10.1021/ja00060a064 | volume=115 | issue=7 | title=First total synthesis of Lycopodium alkaloids of the magellanane group. Enantioselective total syntheses of (-)-magellanine and (+)-magellaninone | year=1993 | journal=Journal of the American Chemical Society | pages=2992–2993 | last1 = Hirst | first1 = Gavin C.}}</ref> It has also been synthesized by the ] group in 1993 at ]<!--Wikipedians do not use "The" as part of Ohio State's name; it is considered a marketing gimmick, and routinely deleted.-->,<ref>{{cite journal|doi=10.1021/ja00090a017 | volume=116 | issue=11 | title=Total Synthesis of the Lycopodium Alkaloids Magellanine and Magellaninone by Three-fold Annulation of 2-Cyclopentenone | year=1994 | journal=Journal of the American Chemical Society | pages=4689–4696 | last1 = Williams | first1 = John P.}}</ref> the Chun-Chen Liao group in 2002 at ],<ref>{{cite journal|doi=10.1002/1521-3773(20021104)41:21<4090::AID-ANIE4090>3.0.CO;2-# | volume=41 | issue=21 | title=Concise and Efficient Total Synthesis of Lycopodium Alkaloid Magellanine | year=2002 | journal=Angewandte Chemie International Edition | pages=4090–4093 | last1 = Yen | first1 = Chi-Feng}}</ref> the Miyuki Ishikazi and Tamiko Takahashi groups in 2005 at the ] and ],<ref>{{cite journal| doi=10.1016/j.tet.2005.02.044 | volume=61 | issue=16 | title=A formal total synthesis of Lycopodium alkaloid, (±)-magellanine, by using the intramolecular Pauson Khand reaction | year=2005 | journal=Tetrahedron | pages=4053–4065 | last1 = Ishizaki | first1 = Miyuki | last2 = Niimi | first2 = Yuka | last3 = Hoshino | first3 = Osamu | last4 = Hara | first4 = Hiroshi | last5 = Takahashi | first5 = Tamiko}}</ref> and the Chisato Mukai group in 2007 at the ].<ref>{{cite journal|doi=10.1002/chin.200818182 | volume=39 | issue=18 | title=ChemInform Abstract: Stereoselective Total Synthesis of Three Lycopodium Alkaloids, (-)-Magellanine (I), (+)-Magellaninone (II), and (+)-Paniculatine (III), Based on Two Pauson—Khand Reactions. | year=2008 | journal=ChemInform | last1 = Kozaka | first1 = Takashi}}</ref> One partial synthesis was completed by the A. I. Meyers group in 1995 at ].<ref>{{cite journal | last1 = Meyers | first1 = A. I. | title = Partial Synthesis | url = http://pubs.rsc.org/en/Content/ArticleLanding/1995/C3/C39950002511 | journal = J. Chem. Soc. Chem. Commun.| volume = 1995 | pages = 2511–2512 }}</ref> |
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Biosynthetically, it is thought to have been derived from ]. This was determined by conducting feeding studies of radiolabeled precursors. <ref>, 2004, 21, 752-772. </ref> |
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Biosynthetically, it is thought to have been derived from ]. This was determined by conducting feeding studies of radiolabeled precursors.<ref>{{cite journal | year = 2004 | title = Biosynthesis of the ''Lycopodium'' Alkaloids | journal = Nat. Prod. Rep. | volume = 21 | pages = 752–772 | doi=10.1039/b409720n | last1 = Ma | first1 = Xiaoqiang | last2 = Gang | first2 = David R.}}</ref> |
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==References== |
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== References == |
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