streptazolin
{{chembox
| ImageFile1 = Streptazolin.svg
| ImageFile2 = Streptazolin space fill.png
| PIN = (2aS,2a1S,3S,4Z)-4-Ethylidene-3-hydroxy-2a,2a1,3,4,6,7-hexahydro-1H-2-oxa-7a-azacyclopenta[cd]inden-1-one
| OtherNames =
|Section1={{Chembox Identifiers
| CASNo = 80152-07-4
| CASNo_Ref = {{Cascite|changed|}}{{cite web |title=KNApSAcK Metabolite Information - C00027639 |url=http://www.knapsackfamily.com/knapsack_core/information.php?word=C00027639 |website=www.knapsackfamily.com}}
| ChemSpiderID = 9944359
| PubChem = 11769676
| SMILES = C=3CCN1C(=O)OC2C1C=3\C(=C\C)\C2O
| StdInChI = 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
| StdInChIKey = OJIUACOQFBQCDF-IKXJTIOISA-N
| ChEMBL = 450203
| ChEBI =
}}
|Section2={{Chembox Properties
| C=11 | H=13 | N=1 | O=3
| MolarMass =
| Appearance =
| Density =
| MeltingPt =
| BoilingPt =
| Solubility = }}
|Section3={{Chembox Hazards
| MainHazards =
| FlashPt =
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Streptazolin is an antibiotic and antifungal substance isolated in 1981 from Streptomyces viridochromogenes.
{{cite journal
| vauthors = Drautz H, Zähner H
| title = Isolation and structure of streptazolin
| journal = Helv. Chim. Acta
| year = 1981
| volume = 64
| issue = 6
| pages = 1752–65
| doi = 10.1002/hlca.19810640605
{{cite journal
| vauthors = Karrer A, Dobler M
| title = Stoffwechselprodukte von Mikroorganismen 217. Mitteilung Röntgenstrukturanalyse von O-Acetyldihydrostreptazolin
| journal = Helv. Chim. Acta
| year = 1982
| volume = 65
| issue = 5
| pages = 1432–35
| doi = 10.1002/hlca.19820650516
}}
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.
{{cite journal
| vauthors = Kozikowski AP, ((Pyeong-uk Park))
| title = Synthesis of 2-substituted .DELTA.3-piperidines: the nitrogen analog of the Ferrier rearrangement. An approach to streptazolin
| journal = J. Org. Chem.
| year = 1984
| volume = 49
| issue = 9
| pages = 1674–1676
| doi =10.1021/jo00183a044
{{cite journal
| author = Kozikowski AP,((Pyeong-uk Park))
| title = Total synthesis of streptazolin - an application of the aza-analogue of the ferrier rearrangement
| journal = J. Am. Chem. Soc.
| year = 1985
| volume = 107
| issue = 6
| pages = 1763–65
| doi = 10.1021/ja00292a054
}}
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