Total syntheses of (.+-.)-. alpha.-and (.+-.)-. beta.-copaene and formal total syntheses of (.+-.)-sativene,(.+-.)-cis-Sativenediol, and (.+-.)-helminthosporal

…, BC Bookser, TS Arrhenius

Index: Wenkert, Ernest; Bookser, Brett C.; Arrbenius, Thomas S. Journal of the American Chemical Society, 1992 , vol. 114, # 2 p. 644 - 654

Full Text: HTML

Citation Number: 21

Abstract

Abstract: Conversion of the previously reported, carvacrol-based 4 (S*)-isopropyl-7 (R*)- chlorobicyclo [3.1. 1] heptan-6-one and its bromo equivalent into (*)-a-and (*)-@-copaene is described. Model S-nor-&copaene was synthesized in the following manner:(a) y- (trimethylsily1) propargyllithium addition,(b) tn-n-butylstannane-induced, dehalogenative, free-radical cyclization and either fluoride-promoted or p-toluenesulfinic acid-catalyzed ...