Synthesis based on cyclohexadienes. Part 21.1 Total synthesis of (±)-hinesol and (±)-10-epi-hinesol

Abstract

An efficient strategy for the construction of the spiro[4.5]decane and eremane systems is described which involves an acid-catalysed rearrangement of an endo alcohol, followed by an oxidative cleavage resulting in the generation of a spiro-system, as the key step. This methodology is extended to the total synthesis of (±)-hinesol and (±)-10-epi-hinesol 2.