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;
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

Streptazolin is an antibiotic and antifungal substance isolated in 1981 from Streptomyces viridochromogenes.[1][2]

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.[1]

The first total synthesis of (racemic) streptazolin was achieved in 1985 with the aid of a modified Ferrier rearrangement.[3][4]

(+)-Dihydrostreptazolin

References

Drautz H, Zähner H (1981). "Isolation and structure of streptazolin". Helv. Chim. Acta. 64 (6): 1752–65. doi:10.1002/hlca.19810640605.
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.
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.
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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[Drautz-1] Drautz H, Zähner H (1981). "Isolation and structure of streptazolin". Helv. Chim. Acta. 64 (6): 1752–65. doi:10.1002/hlca.19810640605.

[Karrer-2] 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.

[Kozikowski1984-3] 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.

[Kozikowski1985-4] 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.