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Synlett 2005(2): 287-288  
DOI: 10.1055/s-2004-837198
LETTER
© Georg Thieme Verlag Stuttgart · New York

An Efficient and Straightforward Synthetic Process to an Amino Sugar Analogue, Furanodictine B

Daisuke Matsuura, Tomoko Nojiri, Yuji Suzuki, Kunihiko Takabe, Hidemi Yoda*
Department of Molecular Science, Faculty of Engineering, Shizuoka University, Johoku 3-5-1, Hamamatsu 432-8561, Japan
Fax: +81(53)4781150; e-Mail: tchyoda@ipc.shizuoka.ac.jp;
Further Information

Publication History

Received 9 November 2004
Publication Date:
17 December 2004 (online)

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Abstract

A convenient and practical strategy for the construction of a natural amino sugar analogue, furanodictine B, isolated from the multicellular fruit body has been developed in an optically active form. The synthetic process is based on readily accessible and stereodefined manipulation of the highly functionalized bicyclic ­derivative incorporating the glucuronolactone-derived skeleton.

Key words

natural product - furanodictine - 3,6-anhydrosugar - ­amino sugar - glucuronolactone

    References

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6

Direct deoxgenation with Et3SiH-Lews acid system after reduction of the lactone 4 to the corresponding lactol derivative, however, resulted in the preparation of the complex mixture.

9

Synthesized furanodictine B in this report was a mixture [α:β = 1:2.4 (natural; α:β = 2:3)1] of the two anomers.