Total Synthesis of (±)-Vibsanin E

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Contents Vol 62(9)

doi:10.1071/CH09267

Total Synthesis of (±)-Vibsanin E

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

^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





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Australian Journal of Chemistry 62(9) 980–982 http://dx.doi.org/10.1071/CH09267
Submitted: 5 May 2009 Accepted: 15 June 2009 Published online: 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.