Total Synthesis of (±)-Vibsanin E

Brett D. Schwartz; Justin R. Denton; Huw M. L. Davies; Craig M. Williams

doi:10.1071/CH09267

RESEARCH FRONT

Previous Next Contents Vol 62(9)

Total Synthesis of (±)-Vibsanin E

Brett D. Schwartz ^A , Justin R. Denton ^B , Huw M. L. Davies ^C ^D and Craig M. Williams ^A ^D

+ Author Affiliations

- Author Affiliations

^A School of Chemistry and Molecular Biosciences, The University of Queensland, Brisbane, Qld 4072, Australia.

^B Department of Chemistry, University at Buffalo, The State University of New York, Buffalo, NY 14260-3000, USA.

^C Department of Chemistry, Emory University, 1515 Dickey Drive, Atlanta, GA, 30322, USA.

^D Corresponding authors. Email: HMDAVIE@emory.edu; c.williams3@uq.edu.au

Australian Journal of Chemistry 62(9) 980-982 https://doi.org/10.1071/CH09267
Submitted: 5 May 2009 Accepted: 15 June 2009 Published: 17 September 2009

Abstract

Vibsanin E (1), a structurally rare complex diterpene, consisting of a compact 3-oxatricyclo[6.3.2.0^5,10] tridecane core and an unprecedented 3,3-dimethylacroyl enol ester functional group, formulate a considerable synthetic challenge. Williams and Davies failed to independently synthesize this nemesis, however, a ‘two heads are better than one’ approach delivered the first total synthesis of the molecule, since its diamond aniversary isolation.

Acknowledgements

We thank The University of Queensland, Australian Research Council (DP0666855) and the National Institutes of Health (GM080337) for financial support. Professor Fukuyama from the Tokushima Bunri University (Japan) is gratefully acknowledged for providing NMR spectra of natural vibsanin E. H.M.L.D. has financial interests in Dirhodium Technologies, Inc., a company that manufactures chiral dirhodium catalysts.

References

Total Synthesis of (±)-Vibsanin E

Abstract

Acknowledgements

Subscriber Login