Oxabicyclo[3.2.1]oct-6-enes as Templates for the Stereoselective Synthesis of Polypropionates: Total Synthesis of Callystatin A and C19-epi-Callystatin A

Mark  Lautens; Timothy A.  Stammers

doi:10.1055/s-2002-34386

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Synthesis 2002(14): 1993-2012
DOI: 10.1055/s-2002-34386

PAPER

Oxabicyclo[3.2.1]oct-6-enes as Templates for the Stereoselective Synthesis of Polypropionates: Total Synthesis of Callystatin A and C19-epi-Callystatin A

Mark Lautens*, Timothy A. Stammers
Davenport Research Laboratories, Department of Chemistry, University of Toronto, Toronto, Ontario, M5S 3H6, Canada
Fax: +1(416)9786083; e-Mail: mlautens@chem.utoronto.ca;

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Publication History

Received 16 June 2002
Publication Date:
26 September 2002 (online)

Abstract
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Abstract

The total synthesis of the polyketide natural product callystatin A and its novel analog C19-epi-callystatin A is described. Our strategy features the use of an enantiomerically pure oxabicyclo[3.2.1]oct-6-ene as a template for the stereocontrolled preparation of the C15-C21 polypropionate region.

Key words

total synthesis - natural products - asymmetric synthesis - ring opening - stereoselectivity

References

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