Cis selective wittig olefination of. ALPHA.-alkoxy ketones and its application to the stereoselective synthesis of plaunotol.

S Inoue, K Honda, N Iwase, K Sato

Index: Inoue; Honda; Iwase; Sato Bulletin of the Chemical Society of Japan, 1990 ,  vol. 63,  # 6  p. 1629 - 1635

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Citation Number: 15

Abstract

Several Wittig olefinations between α-heterosubstituted acetones and a phosphorus ylide were investigated concerning the product stereoselectivity. Benzyloxyacetone and tetrahydropyranyloxyacetone furnished trisubstituted (Z)-olefins exclusively. The stereoselective preparation of oxygenated acyclic terpenoids was practical by use of the direct Wittig olefination toward α-alkoxy ketones, and it facilitated a total synthesis of ...