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Chemistry and biology of diazonamide A: Second total synthesis and biological investigations

Academic Article
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Overview

related to degree

  • Brenzovich, William (Skip), Ph.D. in Chemistry, Scripps Research 2003 - 2008
  • Snyder, Scott, Ph.D. in Chemistry, Scripps Research 1999 - 2004

authors

  • Nicolaou, K.C.
  • Hao, J. L.
  • Reddy, M. V.
  • Rao, P. B.
  • Rassias, G.
  • Snyder, Scott
  • Huang, X. H.
  • Chen, D. Y. K.
  • Brenzovich, William (Skip)
  • Giuseppone, N.
  • Giannakakou, P.
  • O'Brate, A.

publication date

  • 2004

journal

  • Journal of the American Chemical Society  Journal

abstract

  • As an especially unique target for chemical synthesis, diazonamide A has the potential to be constructed through a plethora of synthetic routes, each attended by different challenges and opportunities for discovery. In this article, we detail our second total synthesis of diazonamide A through a sequence entirely distinct from that employed in our first campaign, one whose success required the development of several special strategies and tactics. We also disclose our complete studies regarding the chemical biology of diazonamide A and its structural congeners, and more fully delineate the scope of our protocol for Robinson-Gabriel cyclodehydration using pyridine-buffered POCl(3).

subject areas

  • Antineoplastic Agents
  • Cell Line, Tumor
  • Drug Screening Assays, Antitumor
  • Heterocyclic Compounds with 4 or More Rings
  • Humans
  • Oxazoles
  • Structure-Activity Relationship
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Identity

International Standard Serial Number (ISSN)

  • 0002-7863

Digital Object Identifier (DOI)

  • 10.1021/ja040093a

PubMed ID

  • 15469287
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Additional Document Info

start page

  • 12897

end page

  • 12906

volume

  • 126

issue

  • 40

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