Tetrahedron

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

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

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

全文：HTML全文

被引用次数: 32

摘要

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 ...