Elsevier

Tetrahedron Letters

Volume 48, Issue 9, 26 February 2007, Pages 1563-1566
Tetrahedron Letters

A short and efficient synthesis of 5-hydroxymethylcyclopent-2-enol from d-glucose and its elaboration to the carbanucleoside (−)-carbovir

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Abstract

Introduction of an allyl functionality at C-3 of 1,2:5,6-di-O-isopropylidene-α-d-glucofuranose followed by olefination at C-5 and C-6 provided 1,6-diene 5 which, upon ring closing metathesis and subsequent functional group manipulation, furnished the key cyclopentene diacetate 7, which was elaborated to carbanucleoside (−)-carbovir 1.

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Acknowledgements

The work has been supported by a grant (to S.B.M.) from the Department of Science and Technology (Govt. of India). The authors gratefully acknowledge the Council of Scientific and Industrial Research (CSIR) for providing Research Fellowships (to B.G.R. and P.K.J.) and Emeritus Scientist Scheme (to B.A.).

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