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Total synthesis and structural elucidation of azaspiracid-1. Synthesis-based analysis of originally proposed structures and indication of their non-identity to the natural product

Academic Article
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Overview

related to degree

  • Frederick, Michael, Ph.D. in Chemistry, Scripps Research 2003 - 2008
  • Li, Yiwei, Ph.D. in Organic Chemistry, Scripps Research 1998 - 2003
  • Bernal, Federico, Ph.D. in Chemistry, Scripps Research 1997 - 2002

authors

  • Nicolaou, K.C.
  • Chen, D. Y. K.
  • Li, Yiwei
  • Uesaka, N.
  • Petrovic, G.
  • Koftis, T. V.
  • Bernal, Federico
  • Frederick, Michael
  • Govindasamy, M.
  • Ling, T. T.
  • Pihko, P. M.
  • Tang, W. J.
  • Vyskocil, S.

publication date

  • February 2006

journal

  • Journal of the American Chemical Society  Journal

abstract

  • The key building blocks (6, 7, and 8) for the intended construction of the originally proposed structures of azaspiracid-1, a potent marine-derived neurotoxin, were coupled and the products elaborated to the targeted compounds (1a,b) and their C-20 epimers (2 and 3). The assembly of the three intermediates was accomplished by a dithiane-based coupling reaction that united the C(1)-C(20) (7) and C(21)-C(27) (8) fragments, followed by a Stille-type coupling which allowed the incorporation of the C(28)-C(40) fragment (6) into the growing substrate. Neither of the final products (1a,b) matched the natural substance by TLC or (1)H NMR spectroscopic analysis, suggesting one or more errors in the originally proposed structure for this notorious biotoxin.

subject areas

  • Crystallography, X-Ray
  • Marine Toxins
  • Molecular Structure
  • Spiro Compounds
  • Stereoisomerism
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Identity

International Standard Serial Number (ISSN)

  • 0002-7863

Digital Object Identifier (DOI)

  • 10.1021/ja054748z

PubMed ID

  • 16478179
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Additional Document Info

start page

  • 2258

end page

  • 2267

volume

  • 128

issue

  • 7

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