Chemoselective Nozaki–Hiyama–Takai–Kishi and Grignard reaction: short synthesis of some carbahexopyranoses

Abstract

A common, divergent, efficient, stereoselective and short approach for the total syntheses of some carbahexopyranoses namely, MK7607, (−)-gabosine A, (−)-conduritol E, (−)-conduritol F, 6a-carba-β-D-fructopyranose and other carbasugars using chemoselective Grignard or Nozaki–Hiyama–Takai–Kishi (NHTK) reactions and RCM. Herein, the Grignard and NHTK reactions are able to differentiate the reactivity difference between lactol or lactolacetate and aldehyde of 2 & 6 under given conditions to give the desired skeleton chemoselectivity.