Premium
A method for determination of the absolute stereochemistry of α,β‐epoxy alcohols derived from fatty acid hydroperoxides
Author(s) -
Hamberg Mats
Publication year - 1992
Publication title -
lipids
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.601
H-Index - 120
eISSN - 1558-9307
pISSN - 0024-4201
DOI - 10.1007/bf02535585
Subject(s) - chemistry , absolute configuration , alcohol , epoxide , deoxygenation , allylic rearrangement , derivative (finance) , organic chemistry , epoxy , triphenylphosphine , chirality (physics) , steric effects , stereochemistry , catalysis , financial economics , chiral symmetry breaking , physics , quantum mechanics , nambu–jona lasinio model , quark , economics
A method for the determination of the absolute configuration of the alcohol group of fatty acid α,β‐epoxy alcohols was developed. The method consists of:(i) deoxygenation of the saturated epoxy alcohol to an allylic alcohol by treatment with triphenylphosphine selenide and trifluoroacetic acid; (ii) oxidative ozonolysis of the (−)‐menthoxycarbonyl derivative of the allylic alcohol; and (iii) steric analysis of the resulting 2‐hydroxy acid (methyl ester, (−)‐menthoxycarbonyl derivative) by gas‐liquid chromatography using appropriate reference compounds. The result obtained, coupled with knowledge of the relative configuration of the epoxy alcohol ( erythro/threo ) and of the geometrical configuration of the epoxide group ( cis/trans ), permitted assignment of the absolute configuration of all three asymmetric carbons of the α,β‐epoxy alcohol. The method was applied to the determination of the absolute stereochemistry of two hepoxilins recently isolated from the red alga Murrayella perilados .