Convergent, stereoselective synthesis of the GHIJ fragment of brevetoxin A

Michael T Crimmins; J Lucas Zuccarello; Pamela A Cleary; Jonathan D Parrish

doi:10.1021/ol0526625

Convergent, stereoselective synthesis of the GHIJ fragment of brevetoxin A

Org Lett. 2006 Jan 5;8(1):159-62. doi: 10.1021/ol0526625.

Authors

Michael T Crimmins¹, J Lucas Zuccarello, Pamela A Cleary, Jonathan D Parrish

Affiliation

¹ Venable and Kenan Laboratories of Chemistry, University of North Carolina at Chapel Hill, 27599, USA. [email protected]

PMID: 16381592
DOI: 10.1021/ol0526625

Abstract

[reaction: see text] A stereoselective synthesis of the GHIJ fragment of brevetoxin A utilizing a convergent assembly strategy is described. Glycolate alkylation, ring-closing metathesis, and Hosomi-Sakurai reactions were central operations in the construction of the G ring and J ring subunits, which were united through a Horner-Wadsworth-Emmons coupling. Subsequent dehydrative cyclization produced an endocyclic enol ether that was further elaborated to the tetracyclic GHIJ fragment of brevetoxin A.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

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

Substances

Marine Toxins
Oxocins
Brevetoxin A