Tetrahedron

A general and stereoselective synthesis of the capsaicinoids via the orthoester Claisen rearrangement

H Kaga, K Goto, T Takahashi, M Hino, T Tokuhashi…

Index: Kaga, Harumi; Goto, Kouhei; Takahashi, Tomiki; Hino, Masao; Tokuhashi, Takashi; Orito, Kazuhiko Tetrahedron, 1996 , vol. 52, # 25 p. 8451 - 8470

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Citation Number: 32

Abstract

Capsaicin, a main pungent principle of hot pepper, and its 15 analogs have been efficiently synthesized. The key step of this synthetic sheme is the orthoester Claisen rearrangement, which transformed allylic alcohols 2A-C to (E)-alkenoates 3A-C (EZ> 100) in a highly stereoselective manner. The subsequent carbon chain elongations on 3 based on the cyanation or the malonic acid ester synthesis afforded (E)-alkenoic acids 8, which were ...