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Solution- and soluble-polymer supported asymmetric syntheses of six-membered ring prostanoids

Academic Article
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Overview

authors

  • Lopez-Pelegrin, J. A.
  • Janda, Kim

publication date

  • 2000

journal

  • Chemistry-a European Journal  Journal

abstract

  • An asymmetric synthesis of prostanoids containing a six-membered ring core structure (11a-homoprostaglandins), both in solution and using non-cross-linked polystyrene (NCPS) as a soluble support, was developed. Target molecule 1 was generated in a convergent fashion using a three-component coupling strategy, wherein chiral enone (R)-2 was the precursor of the central ring and the cuprate 3 and triflate 4 were used to introduce the side chains. The chiral center of (R)-2 directed the facial selectivity of the conjugate addition reaction which then dictated the stereochemical outcome of the subsequent alpha alkylation. Attachment of a six-membered ring scaffold to NCPS facilitated purification without compromising synthetic yields, still allowed 1H-NMR analysis of the intermediates in the synthesis, and provided an avenue for the construction of six-membered ring prostanoid libraries.

subject areas

  • Polymers
  • Prostaglandins
  • Solutions
  • Spectrum Analysis
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Research

keywords

  • asymmetric synthesis
  • cuprates
  • polymers
  • prostanoids
  • six-membered rings
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Identity

International Standard Serial Number (ISSN)

  • 0947-6539

Digital Object Identifier (DOI)

  • 10.1002/1521-3765(20000602)6:11<1917::aid-chem1917>3.0.co;2-7

PubMed ID

  • 10894390
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Additional Document Info

start page

  • 1917

end page

  • 1922

volume

  • 6

issue

  • 11

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