Thermal rearrangement of functionalized 6-exo-(1-alkenyl) bicyclo [3.1. 0] hex-2-enes. A total synthesis of (±)-sinularene

E Piers, GL Jung

Index: Piers, Edward; Jung, Grace L. Canadian Journal of Chemistry, 1985 , vol. 63, p. 996 - 998

Full Text: HTML

Citation Number: 11

Abstract

A total synthesis of the racemic form of the marine sesquiterpenoid (-)-sinularene (1) is described. The key step of the synthesis involved the stereoselective thermal rearrangement of the highly functionalized bicyclo [3.1. 0] hexene 12 to provide, in 86% yield, the substituted bicyclo [3.2. 1] octadiene 13. Conversion of the latter substance into (±)- sinularene (1) was accomplished via an efficient 4-step sequence.