Total synthesis of naturally occurring mycolic acids.(E)-and (Z)-threo-2-Docosyl-3-hydroxytetracont-21-enoate

HC Huang, JK Rehmann, GR Gray

Index: Huang, Harry C.; Rehmann, Jill K.; Gray, Gary R. Journal of Organic Chemistry, 1982 , vol. 47, # 21 p. 4018 - 4023

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Citation Number: 10

Abstract

The ethyl esters of (E)-and (Z)-2-docosyl-3-hydroxytetracont-21-enoate (4a and 4b, respectively) have been prepared by a route involving alkylation of the dianion of ethyl 2- docosyl-3-oxobutyrate (2) with either (E)-l-iodo-17-hexatriacontene (144 or (Z)-l-iodo-17- hexatriacontene (134 and subsequent borohydride reduction of the intermediate 8-keto esters (3a and 3b, respectively). Resolution of the 3: 2 mixture of erythro and threo ...