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Antibiotic
Streptazolin
Другие языки:

Streptazolin

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Streptazolin
Streptazolin.svg
Streptazolin space fill.png
Names
Preferred IUPAC name
(2aS,2a1S,3S,4Z)-4-Ethylidene-3-hydroxy-2a,2a1,3,4,6,7-hexahydro-1H-2-oxa-7a-azacyclopenta[cd]inden-1-one
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
PubChem CID
  • 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/s1
    Key: OJIUACOQFBQCDF-IKXJTIOISA-N
  • C=3CCN1C(=O)OC2C1C=3\C(=C\C)\C2O
Properties
C11H13NO3
Molar mass 207.229 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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



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