Volume 31, Issue 7
Natural Products
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ChemInform Abstract: Asymmetric Synthesis of 4′-Methyl-2′,3′-dideoxynucleosides.

Frederick A. Luzzio

Frederick A. Luzzio

Dep. Chem., Univ. Louisville, Louisville, KY 40292, USA

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Alexander V. Mayorov

Alexander V. Mayorov

Dep. Chem., Univ. Louisville, Louisville, KY 40292, USA

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Michael E. Menes

Michael E. Menes

Dep. Chem., Univ. Louisville, Louisville, KY 40292, USA

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First published: 10 June 2010

Abstract

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ChemInform Abstract

Asymmetric stereoselective preparation of a 4-methyl-2,3-dideoxyribose derivative is described which utilizes menthyl pyruvate as a chiral template and an organocerium addition as the key carbon—carbon bond-forming step. This compound (IX) is used as a substrate for a Vorbrueggen pyrimidine glycosylation giving an anomeric mixture of title compounds (X) and (XI).

chemical structure image

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