Volume 29, Issue 1
Natural Products
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ChemInform Abstract: Nucleosides and Nucleotides. Part 165. A Novel Ring-Enlargement Reaction of (3-Oxa-2-silacyclopentyl)methyl Radicals into 4-Oxa-3-silacyclohexyl Radicals. Stereoselective Introduction of a Hydroxyethyl Group via Unusual 6-endo-Cyclization Products Derived from 3-Oxa-4-silahexenyl Radicals and Its Application to the Synthesis of a 4′-α-Branched Nucleoside.

S. SHUTO

S. SHUTO

Fac. Pharm. Sci., Hokkaido Univ., Sapporo 060, Japan

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M. KANAZAKI

M. KANAZAKI

Fac. Pharm. Sci., Hokkaido Univ., Sapporo 060, Japan

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S. ICHIKAWA

S. ICHIKAWA

Fac. Pharm. Sci., Hokkaido Univ., Sapporo 060, Japan

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A. MATSUDA

A. MATSUDA

Fac. Pharm. Sci., Hokkaido Univ., Sapporo 060, Japan

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First published: 24 June 2010

Abstract

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ChemInform Abstract

The title radical reaction with a vinylsilyl tether is applicable to a variety of halohydrins and related compounds for introducing a hydroxyethyl group at the β-position of the hydroxyl with cis-configuration. Reaction conditions are optimized to get the desired products as major compounds.

chemical structure image

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