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Total synthesis of the CP-molecules (CP-263,114 and CP-225,917, phomoidrides B and A). 3. Completion and synthesis of advanced analogues

Academic Article
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Overview

related to degree

  • Baran, Phil, Ph.D. in Chemistry, Scripps Research 1997 - 2001
  • Yoon, Won Hyung, Ph.D. in Chemistry, Scripps Research 1996 - 2001

authors

  • Nicolaou, K.C.
  • Zhong, Y. L.
  • Baran, Phil
  • Jung, J.
  • Choi, H. S.
  • Yoon, Won Hyung

publication date

  • March 2002

journal

  • Journal of the American Chemical Society  Journal

abstract

  • The completion of the total syntheses of the CP-molecules is reported. Several strategies and tactics, including the use of amide-based protecting groups for the homologated C-29 carboxylic acid and the use of an internal pyran protecting group scheme, are discussed. The endeavors leading to the design of new methods for the homologation of hindered aldehydes and to the isolation of a polycyclic byproduct (23), which inspired the development of a new series of reactions based on iodine(V) reagents, are described. In addition, the discovery and development of the LiOH-mediated conversion of CP-263,114 (1) to CP-225,917 (2) is described, and a mechanistic rationale is presented. Finally, a synthetic route to complex analogues of the CP-molecules harboring a maleimide moiety in place of the maleic anhydride is presented.

subject areas

  • Enzyme Inhibitors
  • Maleic Anhydrides
  • Stereoisomerism
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Identity

International Standard Serial Number (ISSN)

  • 0002-7863

Digital Object Identifier (DOI)

  • 10.1021/ja0120126

PubMed ID

  • 11878974
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Additional Document Info

start page

  • 2202

end page

  • 2211

volume

  • 124

issue

  • 10

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