Stereoselective Synthesis of 3,5-Alkadienoic Esters from 2,4-Dienoic Isomers
- 1 April 1988
- journal article
- research article
- Published by Oxford University Press (OUP) in Bulletin of the Chemical Society of Japan
- Vol. 61 (4) , 1410-1412
- https://doi.org/10.1246/bcsj.61.1410
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.Keywords
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