Beilstein Journal of Organic Chemistry (Jul 2011)

Toward an integrated route to the vernonia allenes and related sesquiterpenoids

  • Da Xu,
  • Michael A. Drahl,
  • Lawrence J. Williams

DOI
https://doi.org/10.3762/bjoc.7.104
Journal volume & issue
Vol. 7, no. 1
pp. 937 – 943

Abstract

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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.

Keywords