The Journal of Organic Chemistry

Highly stereoselective total syntheses of. beta.-farnesene,. beta.-sinensal, and dendrolasin employing 2-(hydroxymethyl)-4-(phenylthio)-1-butene as a building block

T Mandai, M Kawada, J Otera

Index: Mandai, Tadakatsu; Kawada, Mikio; Otera, Junzo Journal of Organic Chemistry, 1983 , vol. 48, # 26 p. 5183 - 5185

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Citation Number: 13

Abstract

The we of 2-(hydroxymethyl)-4-(phenylthio)-l-butene (2) for the synthesis of the title compounds is described. The aldehyde 4 obtained by Claisen rearrangement of 2 via a vinyl ether was converted to 5a by 2-propenyllithium. The carboxylic acid 6a was provided by the Claisen rearrangement of 5b via a siloxy vinyl ether. The aldehyde 6d was obtained by reduction of 6a with LiA1H4 followed by oxidation of 6c with NCS-Me2S-Et, N. Treatment ...

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