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Synthesis 2001(11): 1686-1692
DOI: 10.1055/s-2001-16761
PAPER
© Georg Thieme Verlag Stuttgart · New York

A Facile Synthesis of Acyclo-C-nucleoside Analogues from 2(3)-Formylglycals [1]

Ivo Rudloffa, Manfred Michalikb, Alina Monteroa,c, Klaus Peseke*a
a Universität Rostock, Fachbereich Chemie, Buchbinderstr. 9, 18051 Rostock, Germany
Fax: +49(0)3814981763; e-Mail: klaus.peseke@chemie.uni-rostock.de;
b Institut für Organische Katalyseforschung, Buchbinderstraße 5-6, 18055 Rostock, Germany
c Centro de Bioactivos Químicos, Universidad Central de Las Villas, Carretera a Camajuaní, km 5.5. Santa Clara, Cuba
Further Information

Publication History

Received 26 January 2001
Publication Date:
12 August 2004 (online)

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Abstract

The reaction of 2(3)-formylglycals with malononitrile afforded push-pull butadienes with a sugar moiety. The treatment of these branched-chain sugars with ammonia yielded nicotinonitrile acyclo-C-nucleosides. Furthermore, a one step ring transformation of 2(3)-formylglycals with N-aryl-acetoacetanilides to give pyridone acyclo-C-nucleosides is described.

Key words

aldehydes - nucleosides - carbohydrates - formylglycals - push-pull butadienes

1

Presented at the XIXth International Carbohydrate Symposium, San Diego, USA, 1998.

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1

Presented at the XIXth International Carbohydrate Symposium, San Diego, USA, 1998.