Streptazolin

Streptazolin is an antibiotic and antifungal substance isolated in 1981 from Streptomyces viridochromogenes.^[2][3]

Quick facts Names, Identifiers ...

Streptazolin

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
CAS Number	80152-07-4 N[1]
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL450203
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	207.229 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

Close

Because of its tendency to polymerize, 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.^[2]

The first total synthesis of racemic streptazolin was achieved in 1985 with the aid of a modified Ferrier rearrangement.^[4][5]