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Synthesis 2002(16): 2387-2392
DOI: 10.1055/s-2002-35221
PAPER
© Georg Thieme Verlag Stuttgart · New York

A New Laboratory Scale Synthesis for the Anticancer Drug 3′-C-Ethynylcytidine­

Peter S. Ludwig*a, Reto A. Schwendenerb, Herbert Schotta
a University of Tübingen, Institute of Organic Chemistry, Auf der Morgenstelle 18, 72076 Tübingen, Germany
Fax: +49(7121)21716; e-Mail: peter.ludwig@uni-tuebingen.de;
b Paul Scherrer Institute, Division of Medical Radiobiology, 5232 Villingen-PSI, Switzerland
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Publication History

Received 11 July 2002
Publication Date:
04 November 2002 (online)

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Abstract

A new synthetic route for the preparation of larger quantities of the anticancer nucleoside analogue 3′-C-ethynylcytidine is described. Starting from cytidine which was orthogonally protected in three steps, the ketonucleoside analogue as the key intermediate was obtained through oxidation of the unprotected 3′-hydroxy group. Stereoselective addition of the trimethylsilyl-protected acetylide residue at the 3′-carbonyl group followed by a complete deprotection afforded 3′-C-ethynylcytidine in an overall yield of 24% in seven steps.

Key words

drugs - nucleosides - stereoselectivity - ketones - oganometallic ragents