Streptazolin

Streptazolin

Names
IUPAC name (2a1S,6Z,7S,7aS)-6-ethyliden-2a1,3,4,6,7,7a-hexahydro-7-hydroxy-1-oxa-2a-azacyclopenta[cd]inden-2-one
Identifiers
3D model (JSmol)	Interactive image
ChEBI	CHEBI:542525
ChemSpider	9944359
PubChem CID	11769676
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/s1 Key: OJIUACOQFBQCDF-IKXJTIOISA-N
SMILES C=3CCN1C(=O)OC2C1C=3\C(=C\C)\C2O
Properties
Chemical formula	C11H13NO3
Molar mass	207.23 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

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.