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Toward an integrated route to the vernonia allenes and related sesquiterpenoids

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Author(s): Da Xu | Michael A. Drahl | Lawrence J. Williams

Journal: Beilstein Journal of Organic Chemistry
ISSN 1860-5397

Volume: 7;
Issue: 1;
Start page: 937;
Date: 2011;
Original page

Keywords: C–C fragmentation | endocyclic allene | natural product | total synthesis

ABSTRACT
The synthesis of a model endocyclic allene related to the vernonia allenes is described. Fragmentation of a suitable decalin derivative gave the simplified germacrane scaffold. Computational analysis of this and related substrates provides insight into the stereoelectronic requirements of C–C fragmentation. The overall strategy to access these and other sesquiterpenes and the key steps in the present sequence are also discussed.

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Tangokurs Rapperswil-Jona

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