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The continuing saga of the marine polyether biotoxins

Academic Article
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Overview

related to degree

  • Aversa, Robert, Ph.D. in Synthetic Chemistry, Scripps Research 2006 - 2011
  • Frederick, Michael, Ph.D. in Chemistry, Scripps Research 2003 - 2008

authors

  • Nicolaou, K.C.
  • Frederick, Michael
  • Aversa, Robert

publication date

  • 2008

journal

  • Angewandte Chemie-International Edition  Journal

abstract

  • The unprecedented structure of the marine natural product brevetoxin B was elucidated by the research group of Nakanishi and Clardy in 1981. The ladderlike molecular architecture of this fused polyether molecule, its potent toxicity, and fascinating voltage-sensitive sodium channel based mechanism of action immediately captured the imagination of synthetic chemists. Synthetic endeavors resulted in numerous new methods and strategies for the construction of cyclic ethers, and culminated in several impressive total syntheses of this molecule and some of its equally challenging siblings. Of the marine polyethers, maitotoxin is not only the most complex and most toxic of the class, but is also the largest nonpolymeric natural product known to date. This Review begins with a brief history of the isolation of these biotoxins and highlights their biological properties and mechanism of action. Chemical syntheses are then described, with particular emphasis on new methods developed and applied to the total syntheses. The Review ends with a discussion of the, as yet unfinished, story of maitotoxin, and projects into the future of this area of research.

subject areas

  • Animals
  • Ciguatoxins
  • Cyclization
  • Ethers
  • Marine Toxins
  • Molecular Structure
  • Oxocins
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Research

keywords

  • biotoxins
  • maitoxins
  • natural products
  • polyethers
  • total synthesis
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Identity

PubMed Central ID

  • PMC2730226

International Standard Serial Number (ISSN)

  • 1433-7851

Digital Object Identifier (DOI)

  • 10.1002/anie.200801696

PubMed ID

  • 18763702
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Additional Document Info

start page

  • 7182

end page

  • 7225

volume

  • 47

issue

  • 38

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