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Synthesis of ‘Pear Ester’. A novel synthesis of 2,4‐diolefinic aldehydes and esters
Author(s) -
Ohloff Günther,
Pawlak Manfred
Publication year - 1973
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19730560341
Subject(s) - chemistry , pear , wittig reaction , stereospecificity , organic chemistry , formal synthesis , aldehyde , transformation (genetics) , ethyl ester , stereochemistry , catalysis , botany , biochemistry , gene , biology
Vinylogous epoxyaldehydes undergo stereospecific Wittig condensations in high yields. The resulting diolefinic epoxides are cleaved at the C(1)–C(2) single bond, when treated with periodic acid, to give the corresponding aldehydes. Direct transformation into the corresponding ethyl‐ester leads to an efficient synthesis of the ‘pear ester’.