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Enantio- and diastereoselective synthesis of N-acetyl dihydrotetrafibricin methyl ester

Academic Article
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Overview

authors

  • Nuhant, P.
  • Roush, William

publication date

  • April 2013

journal

  • Journal of the American Chemical Society  Journal

abstract

  • A highly diastereoselective synthesis of N-acetyl dihydrotetrafibricin methyl ester (34) is described. The synthesis features three enantioselective double allylboration reactions and an intramolecular hydrosilylation/Fleming-Tamao oxidation sequence to establish seven of the hydroxy-bearing stereocenters of 34. Especially noteworthy is the fragment-assembly double allyboration reaction of 2 and 7 using reagent 3, which provides the advanced intermediate 6 with >20:1 diastereoselectivity.

subject areas

  • Macrolides
  • Molecular Structure
  • Stereoisomerism
  • Streptomyces
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Identity

PubMed Central ID

  • PMC3679187

International Standard Serial Number (ISSN)

  • 0002-7863

Digital Object Identifier (DOI)

  • 10.1021/ja401918r

PubMed ID

  • 23530855
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Additional Document Info

start page

  • 5340

end page

  • 5343

volume

  • 135

issue

  • 14

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