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Total syntheses of (-)-pyrimidoblamic acid and P-3A

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Overview

authors

  • Duerfeldt, A. S.
  • Boger, Dale

publication date

  • February 2014

journal

  • Journal of the American Chemical Society  Journal

abstract

  • Total syntheses of (-)-pyrimidoblamic acid and P-3A are disclosed. Central to the convergent approach is a powerful inverse electron demand Diels-Alder reaction between substituted electron-deficient 1,2,3-triazines and a highly functionalized and chiral primary amidine, which forms the pyrimidine cores and introduces all necessary stereochemistry in a single step. Intrinsic in the convergent approach is the potential it provides for the late stage divergent synthesis of modified analogs bearing deep-seated changes in either the pyrimidine cores or the highly functionalized C2 side chain common to both natural products. The examination of the key cycloaddition reaction revealed that the inherent 1,2,3-triazine mode of cycloaddition (C4/N1 vs C5/N2) as well as the amidine regioselectivity were unaffected by introduction of two electron-withdrawing groups (-CO2R) at C4 and C6 of the 1,2,3-triazine even if C5 is unsubstituted (Me or H), highlighting the synthetic potential of the powerful pyrimidine synthesis.

subject areas

  • Amidines
  • Antineoplastic Agents
  • Bleomycin
  • Cycloaddition Reaction
  • Dipeptides
  • Drug Design
  • Molecular Structure
  • Pyrimidines
  • Triazines
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Identity

PubMed Central ID

  • PMC3940392

International Standard Serial Number (ISSN)

  • 0002-7863

Digital Object Identifier (DOI)

  • 10.1021/ja412298c

PubMed ID

  • 24410439
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Additional Document Info

start page

  • 2119

end page

  • 2125

volume

  • 136

issue

  • 5

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