Reactions of bridgehead halides. A synthesis of modhephene, isomodhephene, and epi-modhephene

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1991-06-01
Authors
Kraus, George
Shi, Jianmin
Kraus, George
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Abstract

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.

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<p>Reprinted (adapted) with permission from <em>The Journal of Organic Chemistry, </em>56(13); 4147-4151. Doi: <a href="http://dx.doi.org/10.1021/jo00013a014" target="_blank">10.1021/jo00013a014</a>. Copyright 1991 American Chemical Society.</p>
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