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Total synthesis of asimicin via highly stereoselective [3 + 2] annulation reactions of substituted allylsilanes

Academic Article
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Overview

authors

  • Tinsley, J. M.
  • Roush, William

publication date

  • August 2005

journal

  • Journal of the American Chemical Society  Journal

abstract

  • A highly stereoselective total synthesis of (+)-asimicin (1) is reported. The synthesis features two chelate-controlled [3 + 2] annulation reactions-one of which (e.g., 2 + 3) constitutes a key, convergent fragment assembly step-that establish all of the stereochemistry of the bis-tetrahydrofuran unit of the natural product.

subject areas

  • Furans
  • Silanes
  • Stereoisomerism
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Identity

International Standard Serial Number (ISSN)

  • 0002-7863

Digital Object Identifier (DOI)

  • 10.1021/ja051986l

PubMed ID

  • 16076173
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Additional Document Info

start page

  • 10818

end page

  • 10819

volume

  • 127

issue

  • 31

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