Syntheses of four D- and L-hoxoses via diastereoselective and enantioselective dihydroxylation reactions

Joel M. Harris, Mark D. Keränen, Hang Nguyen, Victor G. Young, George A. O’Doherty

Research output: Contribution to journalArticlepeer-review

101 Scopus citations

Abstract

An expeditious approach to various protected hexoses has been developed by the use of the Sharpless catalytic asymmetric dihydroxylation reaction. Applying the Sharpless catalytic asymmetric dihydroxylation reaction on vinylfuran, diols with high enantioexcess are produced. The resulting diols can be stereoselectively transformed into either protected D- or L-mannose in five steps and approximately 39% yield from furfural. Similarly, both D- and L-talose and gulose have been synthesized in 19% overall yields, respectively. Using a modified strategy, both protected D- and L-gulo- and allo-sugar-δ-lactones were synthesized in eight steps and ~-20% overall yield from furfural.

Original languageEnglish (US)
Pages (from-to)17-36
Number of pages20
JournalCarbohydrate Research
Volume328
Issue number1
DOIs
StatePublished - Aug 16 2000

Bibliographical note

Funding Information:
We thank the University of Minnesota (Grant-in-Aid program), the ACS for an Institutional Research Grant (IRG-58-001-40-IRG-19), the American Chemical Society–Petroleum Research Fund (ACS–PRF#33953-G1) and the Arnald and Mabel Beckman Foundation for their generous support of our program. We would also like to thank Dr Dirk Friedrich (Hoechst Marion Roussel) for his help in the structure determination of 1a and 13 .

Keywords

  • AD mix
  • Allose
  • Dihydroxylation
  • Enantioselective synthesis
  • Gulose
  • Mannose
  • Sugar lactone
  • Talose
  • Vinylfuran

Fingerprint

Dive into the research topics of 'Syntheses of four D- and L-hoxoses via diastereoselective and enantioselective dihydroxylation reactions'. Together they form a unique fingerprint.

Cite this