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Highly diastereoselective synthesis of pederic acid derivatives

Academic Article
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Overview

authors

  • Roush, William
  • Marron, T. G.
  • Pfeifer, L. A.

publication date

  • February 1997

journal

  • Journal of Organic Chemistry  Journal

abstract

  • A highly diastereoselective synthesis of methyl pederate (2) is described. A critical feature of the successful route is the introduction of the key C(7)-stereocenter at the stage of 4 via an enantioselective, syn-selective aldol reaction of aldehyde 5 and the chiral acyl oxazolidinone 6. Aldehyde 5, in turn, was prepared from the readily available aldol derivative 7 via a chelate-controlled reaction with allyltrimethylsilane. Intermediate 4 was elaborated to 2 via the intermediacy of 7-O-(3,4-dimethoxybenzyl)pederic acid (3), an intermediate in Kishi's syntheses of mycalamides A and B and onnamide A, by way of methyl pyranoside 10 and the fully protected pederic acid derivative 11.
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Identity

International Standard Serial Number (ISSN)

  • 0022-3263

Digital Object Identifier (DOI)

  • 10.1021/jo961841k

PubMed ID

  • 11671436
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Additional Document Info

start page

  • 474

end page

  • 478

volume

  • 62

issue

  • 3

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