Toward an integrated route to the vernonia allenes and related sesquiterpenoids

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 fragme...

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Bibliographic Details
Published in:Beilstein journal of organic chemistry 2011-07, Vol.7 (1), p.937-943
Main Authors: Xu, Da, Drahl, Michael A, Williams, Lawrence J
Format: Article
Language:English
Subjects:
Chemistry
C–C fragmentation
endocyclic allene
Letter
natural product
total synthesis
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Summary: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.
ISSN:1860-5397
1860-5397
DOI:10.3762/bjoc.7.104