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Synthesis 2006(7): 1200-1204  
DOI: 10.1055/s-2006-926375
PAPER
© Georg Thieme Verlag Stuttgart · New York

A New Short and Efficient Route to 3-Deoxy-d-manno-oct-2-ulosonic Acid (KDO) and 3-Deoxy-d-arabino-hept-2-ulosonic Acid (DAH)

Vincent Kikelj, Richard Plantier-Royon*, Charles Portella*
Laboratoire ‘Réactions Sélectives et Applications’, Associé au CNRS (UMR 6519), Université de Reims Champagne-Ardenne, Faculté des Sciences, B. P. 1039, 51687 Reims Cedex 2, France
Fax: +33(3)26913166; e-Mail: charles.portella@univ-reims.fr;
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Publication History

Received 21 October 2005
Publication Date:
08 March 2006 (online)

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Abstract

An efficient synthesis of lactones 5 and 6, known intermediates towards KDO and DAH, respectively, has been achieved by a short and highly efficient route. Homologation of protected d-mannose and d-arabinose was performed by a Peterson reaction with 2-lithio-2-trimethylsilyldithiane or the corresponding bis(methylsulfanyl­) derivative, followed by the cyclization of the resulting ketene dithioacetal under very smooth conditions. An oxidative treatment with iodine gave the lactones 5 and 6 in a three-step sequence with high yields. Interestingly, this approach can be considered as a general method for the synthesis of various 2-deoxy­sugar lactones.

Key words

carbohydrates - natural products - lactones - ketene - dithioacetal