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Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
RESEARCH ARTICLE

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

PK Grant, GP Lynch, J Simpson and G Wong

Australian Journal of Chemistry 46(8) 1125 - 1145
Published: 1993

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.

https://doi.org/10.1071/CH9931125

© CSIRO 1993

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