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

RSC Adv. 2023 Jul 28;13(33):22824-22830. doi: 10.1039/d3ra03704e. eCollection 2023 Jul 26.

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.