THE CHEMISTRY OF LAURENENE .10. A NEW CARBON SKELETON BY REARRANGEMENT OF LAURENAN-2-BETA-OL

Treatment of laurenan-2ݭol (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. © 1990 ASEG.