A formal synthesis of the auriside aglycon

Org Lett. 2008 Jun 5;10(11):2191-4. doi: 10.1021/ol8005908. Epub 2008 May 8.

Abstract

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.

Publication types

  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Acetates / chemistry
  • Aldehydes / chemistry
  • Macrolides / chemical synthesis*
  • Macrolides / chemistry
  • Stereoisomerism
  • Thiazolidines / chemistry

Substances

  • Acetates
  • Aldehydes
  • Macrolides
  • Thiazolidines
  • auriside A
  • auriside B
  • thiazoline-2-thione
  • 3-hydroxybutanal