Stereochemistry of the microbial generation of .delta.-decanolide, .gamma.-dodecanolide, and .gamma.-nonanolide from C18 13-hydroxy, C18 10-hydroxy, and C19 14-hydroxy unsaturated fatty acids
摘要:
(S)-delta-Decanolide (4) was isolated from cultures of Cladosporium suaveolens after the microorganism was fed either (S)- or (R,S)-coriolic acid (1). Feeding (R,S)-10-hydroxyoctadec-(8E)-enoic acid (2) to Yarrowia lipolytica produced (S)-gamma-dodecanolide. When (S)-homocoriolic acid (3) was fed to C.suaveolens, gamma-nonalide slightly enriched in the S enantiomer was produced. At some stage in the biodegradation of 3, an inversion of configuration, from S to R, occurred and was accompanied by the loss of the hydrogen atom originally present on C-14, as GLC/MS analysis of the products of feeding C. suaveolens with dideuterated 10 showed.
Synthesis of the sulfones of leukotriene C4, D4, and E4
作者:Yves Girard、Marie Larue、Thomas R. Jones、Joshua Rokach
DOI:10.1016/s0040-4039(00)87012-4
日期:1982.1
A simple one-steppreparation of the sulfones of Leukotriene C4, D4 and E4 has been developed by the direct oxidation of the parent compounds. An alternative synthesis of these sulfones has also been carried out by reduction of an acetylenic precursor.