The Journal of Organic Chemistry

Total synthesis of (.+-.)-modhephene and its epimer,(.+-.)-epimodhephene

AB Smith III, PJ Jerris

文献索引：Smith, Amos B.; Jerris, Paula J Journal of Organic Chemistry, 1982 , vol. 47, # 10 p. 1845 - 1855

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被引用次数: 54

摘要

This report presents three synthetic approaches to (A)-modhephene (la) and (*)- epimodhephene (18) from enones 10, 11, and 14, the overall yield of modhephene being lo%, 7%, and 1.7%, respectively. The approaches converge upon formation of [3.3. 3] propellenone (9), the latter derived from acid-catalyzed rearrangement of tricyclic octenones 8 and 12. B, yUnsaturated ketones 8 and 12, in turn, were prepared from enones 10 and ...