The Journal of Organic Chemistry

Phospholipid studies of marine organisms. 7. Stereospecific synthesis of (5Z, 9Z)-,(5Z, 9E)-,(5E, 9Z)-, and (5E, 9E)-5, 9-hexacosadienoic acid

PL Mena, O Pilet, C Djerassi

Index: Mena, Philippe L.; Pilet, Olivier; Djerassi, Carl Journal of Organic Chemistry, 1984 , vol. 49, # 18 p. 3260 - 3264

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Citation Number: 23

Abstract

(52, 92)-5, 9-Hexacosadienoic acid (5a) and its stereoisomers 9a, 15a, and 21a were synthesized stereospecifically. The difunctionalized (4Z)-l, l-dimethoxy-8-tosyl-4-octene (2b) prepared by selective ozonolysis of (12, 52)-1, 5-cyclooctadiene (1) was coupled with tridecylmagnesium bromide to afford the cis acetal 3. The corresponding trans acetal 7 was obtained by olefin inversion in 98% stereoisomeric purity. The aldehydes 4 and 8 ...