Exploitation of the vinylogous Wolff rearrangement. An efficient total synthesis of (.+-.)-mayurone,(.+-.)-thujopsene, and (.+-.)-thujopsadiene

SJ Branca, RL Lock, AB Smith III

Index: Branca,S.J. et al. Journal of Organic Chemistry, 1977 , vol. 42, # 19 p. 3165 - 3168

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Citation Number: 21

Abstract

Since the pioneering studies of Arndt and Eistert in the early 1940's a-diazo ketones have found wide application in organic syntheses.'Principal among the synthetically useful reactions of this functionality are the Wolff rearrangement (eq 1) and the intramolecular insertion into olefinic bonds (eq 2). The former transformation can be effected thermally, 2 phot~ chemically,~ and by silver ion1 catalysis, while the latter is best effected by~ opper.~ ...