Streptazolin

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
3D model (JSmol)
ChEMBL
ChemSpider
  • 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
  • C=3CCN1C(=O)OC2C1C=3\C(=C\C)\C2O
Properties
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).

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

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.[2]

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

(+)-Dihydrostreptazolin

References

  1. ^ "KNApSAcK Metabolite Information - C00027639". www.knapsackfamily.com.
  2. ^ a b Drautz H, Zähner H (1981). "Isolation and structure of streptazolin". Helv. Chim. Acta. 64 (6): 1752–65. doi:10.1002/hlca.19810640605.
  3. ^ 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.
  4. ^ 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.
  5. ^ 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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