The Chemistry of Laurenene. X. A New Carbon Skeleton by Rearrangement of Laurenan-2-β-ol

Abstract

Treatment of laurenan-2β-ol (2) with trifluoroacetic acid in dichloromethane at 0° gives as the major product the rearranged alkene (4). This compound has a new carbon-ring system containing three five-membered rings and one six- membered ring. The structure of (4) has been determined by a range of n.m.r. techniques applied to (4) and selected derivatives. Deuterium- labelling experiments have established that the rearrangement proceeds to a remote part of the molecule and then returns to its starting point.