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Synthesis of the C(21)-C(26) fragment of superstolide A: concerning the stereochemistry of (E)-crotylboration reactions of alaninal derivatives

Academic Article
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Overview

authors

  • Yakelis, N. A.
  • Roush, William

publication date

  • May 2003

journal

  • Journal of Organic Chemistry  Journal

abstract

  • A stereoselective synthesis of the C(21)-C(26) fragment of superstolide A has been completed. The absolute and relative stereochemistry of intermediate 14 has been conclusively proven by NMR and X-ray diffraction methods. In the course of this work, it was found that the stereochemistry of 3 had been misassigned in our previously reported synthesis of the C(18)-C(26) segment. This error stems from the unexpected diastereoselectivity in the double asymmetric reaction of N-acetyl-d-alaninal 1 and the tartrate ester modified (E)-crotylboronate (R,R)-2.

subject areas

  • Alanine
  • Catalysis
  • Indicators and Reagents
  • Macrolides
  • Molecular Structure
  • Stereoisomerism
  • Tetrahydronaphthalenes
  • X-Ray Diffraction
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Identity

International Standard Serial Number (ISSN)

  • 0022-3263

Digital Object Identifier (DOI)

  • 10.1021/jo0341012

PubMed ID

  • 12737561
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Additional Document Info

start page

  • 3838

end page

  • 3843

volume

  • 68

issue

  • 10

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