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Synthesis 1999; 1999(2): 341-354
DOI: 10.1055/s-1999-3382
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Back to the Sugars: A New Enantio and Diastereocontrolled Route to Hexoses from Furfural

Miwako Takeuchi* , Takahiko Taniguchi, Kunio Ogasawara
  • *Pharmaceutical Institute, Tohoku University, Aobayama, Sendai 980-8578, Japan; Fax +81(22)2 17 68 45; E-mail: konol@mail.cc.tohoku.ac.jp
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Publikationsdatum:
31. Dezember 1999 (online)

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An integrated enantio and diastereocontrolled route to both enantiomers of the eight possible hexoses has been explored starting from furfural, by employing the Sharpless asymmetric dihydroxylation as a key step. At the present, a route to six of the eight possible hexoses has been established. The present synthesis may be taken as a reversion of the sugar-originated furfural to the sugars via a levoglucosenone, a pyrolysate of cellulose, type intermediate.

asymmetric dihydroxylation - furfural - hexoses - oxidative ring expansion - enantiocontrolled synthesis