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Total synthesis and structural elucidation of azaspiracid-1. Construction of key building blocks for originally proposed structure

Academic Article
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Overview

related to degree

  • Sarlah, David, Ph.D. in Chemistry, Scripps Research 2006 - 2011
  • Frederick, Michael, Ph.D. in Chemistry, Scripps Research 2003 - 2008
  • Bernal, Federico, Ph.D. in Chemistry, Scripps Research 1997 - 2002

authors

  • Nicolaou, K.C.
  • Pihko, P. M.
  • Bernal, Federico
  • Frederick, Michael
  • Qian, W. Y.
  • Uesaka, N.
  • Diedrichs, N.
  • Hinrichs, J.
  • Koftis, T. V.
  • Loizidou, E.
  • Petrovic, G.
  • Rodriquez, M.
  • Sarlah, David
  • Zou, N.

publication date

  • February 2006

journal

  • Journal of the American Chemical Society  Journal

abstract

  • Syntheses of the three key building blocks (65, 98, and 100) required for the total synthesis of the proposed structure of azaspiracid-1 (1a) are described. Key steps include a TMSOTf-induced ring-closing cascade to form the ABC rings of tetracycle 65, a neodymium-catalyzed internal aminal formation for the construction of intermediate 98, and a Nozaki-Hiyama-Kishi coupling to assemble the required carbon chain of fragment 100. The synthesized fragments, obtained stereoselectively in both their enantiomeric forms, were expected to allow for the construction of all four stereoisomers proposed as possible structures of azaspiracid-1 (1a-d), thus allowing the determination of both the relative and absolute stereochemistry of the natural product.

subject areas

  • Crystallography, X-Ray
  • Hydrogen Bonding
  • Marine Toxins
  • Molecular Structure
  • Spiro Compounds
  • Sulfoxides
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Identity

International Standard Serial Number (ISSN)

  • 0002-7863

Digital Object Identifier (DOI)

  • 10.1021/ja0547477

PubMed ID

  • 16478178
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Additional Document Info

start page

  • 2244

end page

  • 2257

volume

  • 128

issue

  • 7

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