Total synthesis of entecavir

J Org Chem. 2013 Jun 7;78(11):5482-91. doi: 10.1021/jo400607v. Epub 2013 May 16.

Abstract

Entecavir (BMS-200475) was synthesized from 4-trimethylsilyl-3-butyn-2-one and acrolein. The key features of its preparation are: (i) a stereoselective boron-aldol reaction to afford the acyclic carbon skeleton of the methylenecylopentane moiety; (ii) its cyclization by a Cp2TiCl-catalyzed intramolecular radical addition of an epoxide to an alkyne; and (iii) the coupling with a purine derivative by a Mitsunobu reaction.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Guanine / analogs & derivatives*
  • Guanine / chemical synthesis
  • Guanine / chemistry
  • Molecular Structure

Substances

  • entecavir
  • Guanine