A Formal Synthesis of the Auriside Aglycon

Rodolfo Tello-Aburto and Horacio F. Olivo
Division of Medicinal and Natural Products Chemistry, The University of Iowa, Iowa City, Iowa 52242
Org. Lett., 2008, 10 (11), pp 2191–2194
DOI: 10.1021/ol8005908
Publication Date (Web): May 8, 2008
Copyright © 2008 American Chemical Society

Abstract

Abstract Image

A highly convergent formal synthesis of the auriside aglycon was achieved. An indene-based thiazolidinethione chiral auxiliary was used for the construction of both the C1−C9 and C10−C17 fragments via acetate aldol reactions. A Meinwald reaction was utilized to install the stereocenter at C2, and a conjugated addition to an ynone was used to construct the C9−C11 enone.

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History

  • Published In Issue June 05, 2008
  • Article ASAPMay 08, 2008
  • Received: March 13, 2008

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