Toward an integrated route to the vernonia allenes and related sesquiterpenoids

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
Main Authors: Da Xu, Michael A. Drahl, Lawrence J. Williams
Format: Article
Language:English
Published: Beilstein-Institut 2011-07-01
Series:Beilstein Journal of Organic Chemistry
Subjects:
C–C fragmentation
endocyclic allene
natural product
total synthesis
Online Access:https://doi.org/10.3762/bjoc.7.104
Description
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

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