Journal of Synthetic Organic Chemistry, Japan
Online ISSN : 1883-6526
Print ISSN : 0037-9980
ISSN-L : 0037-9980
Metal-Assisted Terpenoid Synthesis
Seinosuke OTSUKASusumu AKUTAGAWA
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1981 Volume 39 Issue 12 Pages 1138-1150

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Abstract
Metal-assisted natural product syntheses have been shown and continued to undergo remarkable developments. This account briefly surveys current progress in terpene syntheses based on transition metals. The target products are confined mainly to natural monoterpenes and terpenoids, and the starting materials to isoprene and other abundantly available materials. C-C bond formation reactions, based on oligomerization, telomerization, insertion, and coupling reactions were critically surveyed with respect to their regioselectivity and stereochemistry. Similarly, the introduction, exchange or elimination of a functional group in allylic systems are reviewed. Some functionalized allylic compounds are useful because of their facile allyl transfer (exchange) reactions mediated by palladium. Allylic migrations are notable, especially the enantioselective hydrogen migration of prochiral allylamines. Various other synthetic reactions, including a highly stereospecific epoxidation of olefins, are also described.
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© The Society of Syhthetic Organic Chemistry, Japan
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