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Total synthesis of (+/-)-haouamine A

Academic Article
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Overview

related to degree

  • Burns, Noah Z, Ph.D. in Chemistry, Scripps Research 2004 - 2009

authors

  • Baran, Phil
  • Burns, Noah Z

publication date

  • March 2006

journal

  • Journal of the American Chemical Society  Journal

abstract

  • The first total synthesis of the highly complex and potent anticancer agent haouamine A is reported through an eight-step sequence. Brevity of the sequence and complete control of chemo-, position-, and stereoselectivity (both planar and axial chirality) were possible through the invention of chemistry specifically tailored for the problems at hand, namely a cascade annulation proceeding via a hitherto unknown chemical entity for the indeno-tetrahydropyridine ring system as well as a pyrone-assisted stitching of the daunting bent-aromatic ring.

subject areas

  • Alkylation
  • Animals
  • Crystallography, X-Ray
  • Heterocyclic Compounds with 4 or More Rings
  • Urochordata
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Identity

International Standard Serial Number (ISSN)

  • 0002-7863

Digital Object Identifier (DOI)

  • 10.1021/ja0602997

PubMed ID

  • 16551088
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Additional Document Info

start page

  • 3908

end page

  • 3909

volume

  • 128

issue

  • 12

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