A stereocontrolled method for the synthesis of D- and L-2-deoxy-C-nucleosides using an intramolecular Sakurai-type cyclisation reaction

R.R. Midtkandal; S.J.F. Macdonald; Marie Migaud

doi:10.1039/c0cc00467g

A stereocontrolled method for the synthesis of D- and L-2-deoxy-C-nucleosides using an intramolecular Sakurai-type cyclisation reaction

R.R. Midtkandal, S.J.F. Macdonald, Marie Migaud

School of Pharmacy

Research output: Contribution to journal › Article › peer-review

6 Citations (Scopus)

Abstract

A novel synthetic procedure has been developed that provides access to D/L-2-deoxy-C-nucleosides from 3,4-epoxytetrahydrofuran in seven steps and in moderate to good yields. The key chemical transformation was the Lewis acid catalysed intramolecular cyclisation reaction of an acetal for which the stereochemical outcome was dependent of the reagents' ratio.

Original language	English
Pages (from-to)	4538-4540
Number of pages	3
Journal	Chemical Communications
Volume	46
Issue number	25
DOIs	https://doi.org/10.1039/c0cc00467g
Publication status	Published - 07 Jul 2010

ASJC Scopus subject areas

Catalysis
General Chemistry
Ceramics and Composites
Electronic, Optical and Magnetic Materials
Materials Chemistry
Metals and Alloys
Surfaces, Coatings and Films

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abstract = "A novel synthetic procedure has been developed that provides access to D/L-2-deoxy-C-nucleosides from 3,4-epoxytetrahydrofuran in seven steps and in moderate to good yields. The key chemical transformation was the Lewis acid catalysed intramolecular cyclisation reaction of an acetal for which the stereochemical outcome was dependent of the reagents' ratio.",

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AU - Migaud, Marie

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AB - A novel synthetic procedure has been developed that provides access to D/L-2-deoxy-C-nucleosides from 3,4-epoxytetrahydrofuran in seven steps and in moderate to good yields. The key chemical transformation was the Lewis acid catalysed intramolecular cyclisation reaction of an acetal for which the stereochemical outcome was dependent of the reagents' ratio.

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A stereocontrolled method for the synthesis of D- and L-2-deoxy-C-nucleosides using an intramolecular Sakurai-type cyclisation reaction

Abstract

ASJC Scopus subject areas

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