A versatile strategy for the synthesis of 2,6-disubstituted dihydropyranones

J Org Chem. 2007 May 25;72(11):4280-3. doi: 10.1021/jo070346t. Epub 2007 Apr 21.

Abstract

A concise synthesis of 2,6-disubstituted dihydropyranones was developed. This sequence is based on the Smith three-component dithiane linchpin coupling strategy. By simply switching the order of epoxide addition in the linchpin coupling step, two analogous dihydropyranones were prepared in good yield from the same starting materials. This sequence allows for considerable flexibility in the nature of R(1) and R(2) groups, which facilitates the preparation of a diverse array of 2,6-disubstituted dihydropyranones.

MeSH terms

  • Alkylation
  • Carbohydrates / chemical synthesis*
  • Cyclization
  • Furans / chemistry
  • Pyrones / chemical synthesis*
  • Stereoisomerism

Substances

  • Carbohydrates
  • Furans
  • Pyrones