Regioselective palladium-catalyzed alkylation of allylic halides with benzylic Grignard reagents. Two-step synthesis of abietane terpenes and tetracyclic polyprenoid …

V Rosales, JL Zambrano, M Demuth

Index: Rosales, Viale; Zambrano, Jorge L.; Demuth, Martin Journal of Organic Chemistry, 2002 , vol. 67, # 4 p. 1167 - 1170

Full Text: HTML

Citation Number: 19

Abstract

A highly regioselective palladium-catalyzed α-alkylation of allylic bromides 1a, ce and chloride 1b with substituted and unsubstituted benzylic Grignard reagents is reported. The resulting all-trans polyenehomobenzene derivatives were obtained in excellent yields and regioselectivity. These products were easily converted to abietane-type diterpenes (10-12) and tetracyclic polyprenoid compounds (13, 14) through a Lewis acid-promoted cascade ...