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Enantiospecific total syntheses of kapakahines B and F

Academic Article
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Overview

related to degree

  • Newhouse, Timothy, Ph.D. in Chemistry, Scripps Research 2006 - 2010

authors

  • Newhouse, Timothy
  • Lewis, C. A.
  • Baran, Phil

publication date

  • May 2009

journal

  • Journal of the American Chemical Society  Journal

abstract

  • Gram-scale, enantiospecific total syntheses of the anti-leukemia marine natural products kapakahines B and F have been completed. Two powerfully simplifying transformations have enabled the gram-scale synthesis of this natural product family: (1) an oxidative N-C bond-forming reaction that sets a key quaternary center with complete stereocontrol and (2) a unique strategy for the construction of twisted macrocycles via dynamic equilibration of complex late-stage intermediates.

subject areas

  • Antineoplastic Agents
  • Biological Products
  • Macrocyclic Compounds
  • Peptides, Cyclic
  • Quaternary Ammonium Compounds
  • Stereoisomerism
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Identity

International Standard Serial Number (ISSN)

  • 0002-7863

Digital Object Identifier (DOI)

  • 10.1021/ja901573x

PubMed ID

  • 19374357
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Additional Document Info

start page

  • 6360

end page

  • 6361

volume

  • 131

issue

  • 18

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