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Stereospecific synthesis of cis and trans fatty esters
Author(s) -
Rakoff Henry,
Emken Edward A.
Publication year - 1977
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/bf02570909
Subject(s) - chemistry , stereospecificity , cis–trans isomerism , diastereomer , stereochemistry , triethyl orthoformate , organic chemistry , catalysis
Abstract The erythro and threo isomers of methyl 9,10‐dihydroxyoctadecanoate and the threo isomer of methyl 12,13‐dihydroxy‐ cis ‐9‐octadecenoate were converted into methyl cis ‐ and trans ‐9‐octadecenoate and methyl cis ‐9, rans ‐12‐octadecadienoate, respectively, by reaction of the dihydroxy ester with triethyl orthoformate to give the 2‐ethoxy‐1,3‐dioxolane which was thermally decomposed to the unsaturated ester.