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Streptazolin

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Streptazolin
Names
Preferred IUPAC name (2aS,2aS,3S,4Z)-4-Ethylidene-3-hydroxy-2a,2a,3,4,6,7-hexahydro-1H-2-oxa-7a-azacyclopentainden-1-one
Identifiers
CAS Number
3D model (JSmol)
ChEMBL
ChemSpider
PubChem CID
InChI
  • InChI=1S/C11H13NO3/c1-2-6-7-4-3-5-12-8(7)10(9(6)13)15-11(12)14/h2,4, 8-10,13H,3,5H2,1H3/b6-2-/t8-,9-,10-/m0/s1Key: OJIUACOQFBQCDF-IKXJTIOISA-N
SMILES
  • C=3CCN1C(=O)OC2C1C=3\C(=C\C)\C2O
Properties
Chemical formula C11H13NO3
Molar mass 207.229 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

Streptazolin is an antibiotic and antifungal substance isolated in 1981 from Streptomyces viridochromogenes.

Because of its polymerisation tendency, it is not suitable for therapeutic use. 1,4-reduction of the conjugated diene gives dihydrostreptazolin which is stable, but has very limited antimicrobial properties.

The first total synthesis of (racemic) streptazolin was achieved in 1985 with the aid of a modified Ferrier rearrangement.

(+)-Dihydrostreptazolin

References

  1. "KNApSAcK Metabolite Information - C00027639". www.knapsackfamily.com.
  2. ^ Drautz H, Zähner H (1981). "Isolation and structure of streptazolin". Helv. Chim. Acta. 64 (6): 1752–65. doi:10.1002/hlca.19810640605.
  3. Karrer A, Dobler M (1982). "Stoffwechselprodukte von Mikroorganismen 217. Mitteilung Röntgenstrukturanalyse von O-Acetyldihydrostreptazolin". Helv. Chim. Acta. 65 (5): 1432–35. doi:10.1002/hlca.19820650516.
  4. Kozikowski AP, Pyeong-uk Park (1984). "Synthesis of 2-substituted .DELTA.3-piperidines: the nitrogen analog of the Ferrier rearrangement. An approach to streptazolin". J. Org. Chem. 49 (9): 1674–1676. doi:10.1021/jo00183a044.
  5. Kozikowski AP,((Pyeong-uk Park)) (1985). "Total synthesis of streptazolin - an application of the aza-analogue of the ferrier rearrangement". J. Am. Chem. Soc. 107 (6): 1763–65. doi:10.1021/ja00292a054.


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