BORON-TRIFLUORIDE CATALYZED REARRANGEMENTS OF NOVEL EPOXIDE DERIVATIVES OF MANOOL AND MANOYL OXIDE

Authors
GRANT PK LYNCH GP SIMPSON J WONG G
Citation
Pk. Grant et al., BORON-TRIFLUORIDE CATALYZED REARRANGEMENTS OF NOVEL EPOXIDE DERIVATIVES OF MANOOL AND MANOYL OXIDE, Australian Journal of Chemistry, 46(8), 1993, pp. 1125-1145
Citations number
20
Categorie Soggetti
Chemistry
Journal title
Australian Journal of Chemistry → ACNP
ISSN journal
00049425
Volume
46
Issue
8
Year of publication
1993
Pages
1125 - 1145
Database
ISI
SICI code
0004-9425(1993)46:8<1125:BCRONE>2.0.ZU;2-3
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 diosphenol s is reported. Lewis acid promoted intramolecular rearrangements of th ese were investigated. Reaction of epoxide (1) with boron trifluoride etherate resulted in the isolation of a novel dimer (44), the structur e being elucidated by X-ray crystallography. However, epoxides (2)-(4) yielded monomeric rearrangement products.