Volume 28, Issue 50
Natural Products
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ChemInform Abstract: (1S,2R)-((Benzyloxy)methyl)cyclopent-3-enol. A Versatile Synthon for the Preparation of 4′,1′a-Methano- and 1′,1′a-Methanocarbocyclic Nucleosides.

A. EZZITOUNI

A. EZZITOUNI

Lab. Med. Chem., Natl. Cancer Inst., NIH, Bethesda, MD 20892, USA

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P. RUSS

P. RUSS

Lab. Med. Chem., Natl. Cancer Inst., NIH, Bethesda, MD 20892, USA

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V. E. MARQUEZ

V. E. MARQUEZ

Lab. Med. Chem., Natl. Cancer Inst., NIH, Bethesda, MD 20892, USA

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First published: 02 August 2010

Abstract

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ChemInform Abstract

The key steps in the synthesis of the 4′,1′a-methanocarbocyclic nucleoside (XII) from the title enol (I) are regio- and stereoselective azidoselenylation of the olefin (I) and Simons-Smith cyclopropanation of the olefin (VII). Formation of a 1′,1′a- methanocarbocyclic nucleoside from (I) is previously reported.

chemical structure image

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