The Chemistry of Laurenene. XI. A Deep-Seated Rearrangement of the Laurenane Skeleton

Abstract

A trifluoroacetic acid induced rearrangement product of laurenan-2β-ol (3) has been shown to have the 4H-pentaleno[6a,1-c]indene skeleton. This combination of one six- membered ring and three five-membered rings has been encountered once previously, again as a rearrangement product of the laurenane skeleton. The structure was determined by n.m.r. studies and by X-ray crystallography conducted primarily on a stable ozonide (6).