Stereoselective protecting group free synthesis of D,L-gulose ethyl glycoside via multicomponent enyne cross metathesis--hetero Diels-Alder reaction

Carbohydr Res. 2009 Jul 27;344(11):1285-8. doi: 10.1016/j.carres.2009.05.007. Epub 2009 May 9.

Abstract

An efficient and stereoselective synthesis of D,L-gulose was described. The key step of the synthetic route is represented by a multicomponent enyne cross metathesis-hetero Diels-Alder reaction which allows the formation of the pyran ring from cheap and commercially available substrates in a single synthetic step. The synthesis of D,L-gulose was accomplished without the use of protecting groups making this approach highly desirable also in terms of atom economy.

MeSH terms

  • Glycosides / chemical synthesis*
  • Glycosides / chemistry
  • Microwaves
  • Stereoisomerism
  • Substrate Specificity

Substances

  • Glycosides
  • ethyl guloside