Boron Trifluoride Catalyzed Rearrangements of Novel Epoxide Derivatives of Manool and Manoyl Oxide

Abstract

The preparation of four epoxides (1)-(4) derived from manool [labda-8(17),14-dien-13-ol] and manoyl oxide (8,13-epoxylabdane) via diosphenols is reported. Lewis acid promoted intramolecular rearrangements of these were investigated. Reaction of epoxide (1) with boron trifluoride etherate resulted in the isolation of a novel dimer (44), the structure being elucidated by X-ray crystallography. However, epoxides (2)-(4) yielded monomeric rearrangement products.