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Letter

Improved Synthesis of the ABCDE Fragment of Brevetoxin A

Supporting Info

Michael T. Crimmins,* Patrick J. McDougall, and J. Michael Ellis

Venable and Kenan Laboratories of Chemistry, University of North Carolina at Chapel Hill, Chapel Hill, North Carolina 27599

Org. Lett., 2006, 8 (18), pp 4079–4082

DOI: 10.1021/ol0615782

Publication Date (Web): August 4, 2006

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

Abstract

A second-generation synthesis of the BCDE fragment of brevetoxin A is described. Novel reactions were developed that extend the utility of the asymmetric glycolate alkylation reaction and improve scale-up to provide gram quantities of the B and E subunits. Significant improvements to the convergent assembly of the tetracycle were also realized. In addition, formation of the A ring lactone was accomplished to complete the ABCDE pentacycle.

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Published In Issue August 31, 2006
Received June 27, 2006

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Letter

Improved Synthesis of the ABCDE Fragment of Brevetoxin A

Abstract

Available Supporting Information for This Article

PDF

Tools

SciFinder Links

History

Recommend & Share

Related Content

Nine-Step Enantioselective Total Synthesis of (+)-Minfiensine

A Short Enantioselective Total Synthesis of the Fundamental Pentacyclic Triterpene Lupeol

Studies for the Synthesis of Xenicane Diterpenes. A Stereocontrolled Total Synthesis of 4-Hydroxydictyolactone

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