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化学选择性的野崎-日山-高井-岸反应及格氏反应:某些碳杂己吡喃糖的简短合成

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

作者信息

Vinaykumar Allam, Surender Banothu, Rao Batchu Venkateswara

机构信息

Fluoro-Agrochemicals, CSIR-Indian Institute of Chemical Technology Hyderabad India

Organic Synthesis and Process Chemistry, CSIR-Indian Institute of Chemical Technology Hyderabad India

出版信息

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.

摘要

一种通用、多样、高效、立体选择性且简短的方法,用于某些碳杂己吡喃糖(即MK7607、(-)-加波辛A、(-)-康杜立醇E、(-)-康杜立醇F、6a-碳杂-β-D-果糖吡喃糖及其他碳杂糖)的全合成,该方法使用化学选择性格氏反应或野崎-桧山-高木-岸石(NHTK)反应以及关环复分解反应(RCM)。在此,格氏反应和NHTK反应能够在给定条件下区分2位和6位的内醇或内醇乙酸酯与醛之间的反应活性差异,从而实现所需骨架的化学选择性。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f895/10375257/f519a3796f8d/d3ra03704e-f1.jpg

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