Reagent-Controlled Divergent Synthesis of C-Glycosides

J Org Chem. 2020 Sep 4;85(17):11449-11464. doi: 10.1021/acs.joc.0c01544. Epub 2020 Aug 24.

Abstract

By turning on or switching off the directing effect of the C3-OH-located o-diphenylphosphanylbenzoyl (o-DPPB) group in glycals, a reagent-controlled protocol for divergent and regio- and stereoselective syntheses of C-glycosides has been established. In particular, the silence of the directing effect of o-DPPB was achieved by the introduction of a ZnCl2 additive, which is operationally simple and efficient. The flexibility of the novel protocol was exhibited not only by the easy access of both α- and β-C-glycosides but also by the versatility of the obtained formal Ferrier rearrangement products, which can be easily derivatized to various C-glycoside analogues owing to the embedded multifunctionalities.

Publication types

  • Research Support, Non-U.S. Gov't