Intramolecular Tishchenko Reactions of Protected Hexos-5-uloses: a Novel and Efficient Synthesis of l-Idose and l-Altrose

M. Adinolfi; G. Barone; F. De Lorenzo; A. Iadonisi

doi:10.1055/s-1999-3156

Synlett 1999; 1999(3): 336-338
DOI: 10.1055/s-1999-3156

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Intramolecular Tishchenko Reactions of Protected Hexos-5-uloses: a Novel and Efficient Synthesis of l-Idose and l-Altrose

M. Adinolfi^* , G. Barone, F. De Lorenzo, A. Iadonisi

^*Dipartimento di Chimica Organica e Biologica, Università degli Studi Federico II, Via Mezzocannone 16, I-80134 Napoli, Italy; Fax +39 08 15 52 12 17; E-mail: iadonisi@unina.it

Abstract

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Protected t-butyl esters of aldonic acids with the rare L-ido and L-altro configuration can be effectively obtained by a diastereoselective Tishchenko reaction of hexos-5-uloses induced by t-BuOSmI₂. These compounds can be easily converted into the corresponding protected lactones and free sugars.

Tishchenko reaction - trivalent samarium reagents - L-idose - L-altrose - aldonic acids t-butyl esters

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