Enantioselective synthesis of alpha-methylene-beta-hydroxy carboxylic acid derivatives via a diastereoselective aldol/beta-elimination sequence: application to the C(15)-C(21) fragment of tedanolide C

Org Lett. 2010 May 21;12(10):2342-5. doi: 10.1021/ol1006955.

Abstract

An enantioselective synthesis of alpha-methylene-beta-hydroxy carboxylic acid derivatives via a highly diastereoselective, one-pot syn-aldol and beta-elimination sequence utilizing the chiral beta-(phenylselenyl)propionyl imide 15 is described. This new method, which constitutes an alternative to the Baylis-Hillman reaction, has been applied to the synthesis of the C(15)-C(21) fragment of tedanolide C.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Carboxylic Acids / chemical synthesis*
  • Carboxylic Acids / chemistry
  • Imides / chemistry*
  • Ketones / chemistry*
  • Macrolides / chemical synthesis*
  • Macrolides / chemistry
  • Molecular Conformation
  • Stereoisomerism

Substances

  • Carboxylic Acids
  • Imides
  • Ketones
  • Macrolides
  • tedanolide C