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Communication | Special issue | Vol 61, No. 1, 2003, pp.87-92
Published online: 6th October, 2003
DOI: 10.3987/COM-03-S46
Enantioselective Synthesis of the G-Ring of Brevetoxin A

Michael T. Crimmins* and Pamela A. Cleary

*Department of Chemistry, CB 3290, University of North Carolina at Chapel Hill, Chapel Hill, NC 27599-3290, U.S.A.

Abstract

An enantioselective synthesis of the eight-membered G-ring of brevetoxin A is described. The synthesis exploits a ring-closing metathesis reaction to construct the eight-membered ether ring. The stereochemistry of the α and α’ centers of the ether linkage were established through a Sharpless kinetic resolution and an asymmetric glycolate alkylation reaction.

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