Reactions of bridgehead halides. A synthesis of modhephene, isomodhephene, and epi-modhephene
Is Version Of
A Synthesis of modhephene has been achieved, the key feature of which is the use of a novel nucleophilic addition/rearrangement reaction to develop the carbon framework. Stereochemical control of the stereogenic center bearing the methyl group was accomplished by variation of the hydrogenation conditions. As a byproduct of this work, we have clarified structural assignments of intermediates from previous syntheses.
Reprinted (adapted) with permission from The Journal of Organic Chemistry, 56(13); 4147-4151. Doi: 10.1021/jo00013a014. Copyright 1991 American Chemical Society.