Stereoselective synthesis of 3, 5-alkadienoic esters from 2, 4-dienoic isomers

…, J Sakamoto, A Kuroda, M Utaka, A Takeda

Index: Tsuboi, Sadao; Sakamoto, Jun-ichi; Kuroda, Akihisa; Utaka, Masanori; Takeda, Akira Bulletin of the Chemical Society of Japan, 1988 , vol. 61, p. 1410 - 1412

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Citation Number: 8

Abstract

The treatment of (2E, 4Z)-2, 4-alkadienoic esters with lithium diisopropylamide (LDA) at− 80° C gave (3E, 5E)-isomers with 81–98% stereoselectivity. In contrast, the treatment of (2E, 4E)- isomers under the same conditions gave (3E, 5Z)-isomers with 72–80% stereoselectivity. The application to the synthesis of megatomoic acid is described. Carbon-13 NMR data regarding these 3, 5-dienoates were obtained.