Enantiospecific synthesis of tricyclo[5.2.1.04,8]decanes via acid catalysed rearrangement of isotwistanes

An acid catalysed rearrangement was employed for the enantiospecific conversion of isotwistanol to tricyclo[5.2.1.04,8]decanes, which provided support for the proposed biosynthesis of allopupukeananes from pupukeananes. The strategy has been further extended to the enantiospecific synthesis of a homobrexane.