Improved synthesis of the ABCDE fragment of brevetoxin A

Michael T Crimmins; Patrick J McDougall; J Michael Ellis

doi:10.1021/ol0615782

Improved synthesis of the ABCDE fragment of brevetoxin A

Org Lett. 2006 Aug 31;8(18):4079-82. doi: 10.1021/ol0615782.

Authors

Michael T Crimmins¹, Patrick J McDougall, J Michael Ellis

Affiliation

¹ Venable and Kenan Laboratories of Chemistry, University of North Carolina at Chapel Hill, Chapel Hill, NC 27599, USA. crimmins@email.unc.edu

PMID: 16928078
DOI: 10.1021/ol0615782

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.

Publication types

Research Support, N.I.H., Extramural

MeSH terms

Marine Toxins / chemical synthesis*
Molecular Structure
Oxocins / chemical synthesis*

Substances

Marine Toxins
Oxocins
Brevetoxin A

Grants and funding

GM 60567/GM/NIGMS NIH HHS/United States