A regio- and stereocontrolled approach to pyranosyl C-nucleoside synthesis

Philip Redpath; Simon Macdonald; Marie E Migaud

doi:10.1021/ol801183e

A regio- and stereocontrolled approach to pyranosyl C-nucleoside synthesis

Org Lett. 2008 Aug 7;10(15):3323-6. doi: 10.1021/ol801183e. Epub 2008 Jul 4.

Authors

Philip Redpath¹, Simon Macdonald, Marie E Migaud

Affiliation

¹ Respiratory CEDD, Stevenage SG12NY, UK.

PMID: 18598053
DOI: 10.1021/ol801183e

Abstract

Six novel diastereomerically pure C-nucleosides have been synthesized from nonchiral starting materials, using the ene/intramolecular Sakurai cyclization reaction demonstrating a simple, general, and stereocontrolled approach to pyranosyl C-nucleosides.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Molecular Conformation
Nucleosides / chemical synthesis*
Pyrans / chemical synthesis*
Stereoisomerism

Substances

Nucleosides
Pyrans