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Synthesis 2011(8): 1290-1294  
DOI: 10.1055/s-0030-1258475
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Novel Concise Synthesis of (±)-Noviose and l-(+)-Noviose by Palladium-Catalyzed Epoxide Opening

Yoshitaka Matsushima*, Jun Kino
Department of Chemistry, Hamamatsu University School of Medicine, Handayama, Hamamatsu 431-3192, Japan
Fax: +81(53)4352319; e-Mail: ymatsu@hama-med.ac.jp;
Further Information

Publication History

Received 28 December 2010
Publication Date:
14 March 2011 (online)

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Abstract

We established a novel, concise synthetic route for obtaining noviose, the deoxy sugar component of aminocoumarin antibiotics. l-(+)-Noviose was successfully synthesized by utilizing a palladium-catalyzed epoxide-opening reaction and the subsequent lactone formation as key reactions, starting from a nonsugar chiral epoxide, which is easily available in both enantiomeric forms.

Key words

noviose - novobiocin - aminocoumarin antibiotics - palladium-catalyzed epoxide opening

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20

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