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Studies toward the total synthesis of sorangiolides and their analogues. A convergent stereoselective synthesis of the macrocyclic lactone precursors

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Overview

authors

  • Das, S.
  • Abraham, S.
  • Sinha, Subhash

publication date

  • June 2007

journal

  • Organic Letters  Journal

abstract

  • Stereoselective synthesis of the fully protected 18-membered macrocyclic lactones as the immediate precursors of the natural products, sorangiolides A and B, is described. The key steps used in the synthesis include the sp3-hybridized carbon-carbon Fu cross coupling, the stereoselective Evans' aldol reaction with 1,5-anti induction, the 1,3-diastereoselective syn reduction of a beta-hydroxyketone intermediate, and Mukaiyama macrolactonization reactions.

subject areas

  • Lactones
  • Lauric Acids
  • Macrocyclic Compounds
  • Molecular Structure
  • Stereoisomerism
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Identity

International Standard Serial Number (ISSN)

  • 1523-7060

Digital Object Identifier (DOI)

  • 10.1021/ol070517g

PubMed ID

  • 17503834
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Additional Document Info

start page

  • 2273

end page

  • 2276

volume

  • 9

issue

  • 12

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