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Diastereoselective synthesis of the endo- and exo-spirotetronate subunits of the quartromicins. The first enantioselective Diels-Alder reaction of an acyclic (Z)-1,3-diene

Academic Article
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Overview

authors

  • Roush, William
  • Limberakis, C.
  • Kunz, R. K.
  • Barda, D. A.

publication date

  • 2002

journal

  • Organic Letters  Journal

abstract

  • [reaction: see text]. Diastereoselective syntheses of the endo- and exo-spirotetronates 1 and 2, corresponding to the galacto and agalacto fragments of quartromicins A3 and D3, are described. The key step of these syntheses are highly enantio- and diastereoselective Lewis acid catalyzed Diels-Alder reactions of the 1,1,3,4-tetrasubstituted diene 3.

subject areas

  • Catalysis
  • Furans
  • Molecular Conformation
  • Spiro Compounds
  • Stereoisomerism
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Identity

International Standard Serial Number (ISSN)

  • 1523-7060

Digital Object Identifier (DOI)

  • 10.1021/ol025772+

PubMed ID

  • 11975624
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Additional Document Info

start page

  • 1543

end page

  • 1546

volume

  • 4

issue

  • 9

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