Abstract
Acetals (1) and (2), analogous to the valued perfumery acetals (3) and (4), have been synthesized from manool (5) for structure/odour
comparison. Selenoxide elimination gave diene (13)
which underwent Cope rearrangement and selective epoxidation to give the 8β,9β-epoxide
(19). Borontrifluoride-catalysed rearrangement
established this stereochemistry and led by selective oxymercuration
of diene (24) to the required acetals.
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