The analytical approach to synthesis : Twistane

Abstract

A detailed analysis, for synthetic purposes, of the structure of twistane is given. It is hoped that this will serve, for teaching purposes, to illustrate the concept of the analytical approach to synthesis. A description of the synthesis of 3-oxobicyclo[3,3,l]nonan-6-ylmethyl methanesulphonate and its cyclization to twistan-4-one and an isomer, tricyclo[3,3,1,1^4,6]decan-3-one, is given. This synthesis illustrates the remaining single-bond process for constructing the twistane skeleton.