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

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...

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Detalles Bibliográficos
Autores principales: Vinaykumar, Allam, Surender, Banothu, Rao, Batchu Venkateswara
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2023
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10375257/
https://www.ncbi.nlm.nih.gov/pubmed/37520087
http://dx.doi.org/10.1039/d3ra03704e
Descripción
Sumario: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.

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