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
ChEBI CHEBI:542525
ChEMBL ChEMBL450203
ChemSpider 9944359
Jmol interactive 3D Image
PubChem 11769676
Properties
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.[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.<ref name=" name="Drautz" />

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

(+)-Dihydrostreptazolin

References

  1. Drautz, H, Zähner, H (1981). "Isolation and structure of streptazolin". Helv. Chim. Act. 64 (6): 1752–65. doi:10.1002/hlca.19810640605.
  2. Karrer, A, Dobler, M (1982). "Stoffwechselprodukte von Mikroorganismen 217. Mitteilung Röntgenstrukturanalyse von O-Acetyldihydrostreptazolin". Helv. Chim. Act. 65 (5): 1432–35. doi:10.1002/hlca.19820650516.
  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.
  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.


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