Syntheses of Cecropia Juvenile Hormones by Selective Side-chain Methylation of (E, E)-Farnesol

A Yasuda, S Tanaka, H Yamamoto…

Index: Yasuda; Tanaka; Yamamoto; Nozaki Bulletin of the Chemical Society of Japan, 1979 , vol. 52, # 6 p. 1701 - 1704

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Citation Number: 19

Abstract

The stereoselective route to the title insect hormones (JH-1 & JH-2) depends crucially on the epoxidation of allylic alcohols with t-butyl hydroperoxide in the presence of oxobis (2, 4- pentanedionato-O, O′) vanadium (IV). The oxidation of 2-methyl-1-hepten-3-ol exclusively produces the (2R*, 3S*) isomerofthe diastereomeric epoxy alcohols. This is converted into (Z)-6-methyl-5-undecene by the sequence involving oxirane reaction with lithium ...

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