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Concerning the synthesis of the tedanolide C(13)-C(23) fragment via anti-aldol reaction

Academic Article
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Overview

authors

  • Dunetz, J. R.
  • Roush, William

publication date

  • May 2008

journal

  • Organic Letters  Journal

abstract

  • Synthesis of C(13)-C(23) aldehyde 4, an important intermediate in a planned total synthesis of tedanolide, is described. The stereoselectivity of the key anti-aldol reaction of aldehyde 5 and ketone 6 (en route to 4) perfectly tracks the enantiomeric purity of 5. It is demonstrated that aldehyde 24, a precursor of 5, undergoes facile epimerization during a Swern oxidation and stabilized ylide olefination sequence.

subject areas

  • Aldehydes
  • Ketones
  • Lactones
  • Macrolides
  • Molecular Structure
  • Stereoisomerism
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Identity

International Standard Serial Number (ISSN)

  • 1523-7060

Digital Object Identifier (DOI)

  • 10.1021/ol800546g

PubMed ID

  • 18422319
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Additional Document Info

start page

  • 2059

end page

  • 2062

volume

  • 10

issue

  • 10

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