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Synlett 2002(6): 0891-0894
DOI: 10.1055/s-2002-31900
LETTER
© Georg Thieme Verlag Stuttgart · New York

Stereodivergent Synthesis of Carbasugars from d-Mannose. Syntheses of 5a-Carba-α-d-allose, β-l-Talose, and α-l-Gulose Pentaacetates

Ana M. Gómez*, Eduardo Moreno, Serafín Valverde, J. Cristóbal López*
Instituto de Química Orgánica General, CSIC, Juan de la Cierva 3, 28006 Madrid, Spain
Fax: +34(91)5644853; e-Mail: clopez@iqog.csic.es;
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Publication History

Received 15 April 2002
Publication Date:
07 February 2007 (online)

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Abstract

A stereodivergent entry to 5a-carba-d- and l-pyranoses from a single precursor is described. The approach is based on the selective deoxygenation of polyoxygenated methylcyclohexane intermediates, readily available from radical cyclization of d-mannose derivatives. This strategy has been applied to the preparation of 5a-carba-α-d-allo-, 5a-carba-β-l-talo-, and 5a-carba-α-l-gulopyranose pentaacetates.

Key words

stereodivergent synthesis - carbasugars - radical cycli-zation - stereoselective synthesis