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Synthesis of 2,6-Dideoxysugars via Ring-Closing Olefinic Metathesis
 

Summary: Synthesis of 2,6-Dideoxysugars via
Ring-Closing Olefinic Metathesis
Peter R. Andreana, Jason S. McLellan, Yongchen Chen, and Peng George Wang*
Department of Chemistry, Wayne State UniVersity, Detroit, Michigan
pwang@chem.wayne.edu
Received August 9, 2002
ABSTRACT
Grubbs' RuCl2(dCHPh)(PCy3)2 (catalyst 1) and RuCl2(dCHPh)(PCy3)(IMess) (catalyst 2) complexes have been successfully utilized in the
construction of ,-unsaturated -lactones containing various substitution patterns of methyl groups. Asymmetric dihydroxylation followed
by reduction leads to 3,4-cis-dihydroxy-2,6-dideoxypyranoses, which have proven to play very important biological roles as key components
of natural products.
The ring-closing metathesis (RCM) reaction continues to play
a powerful role in the construction of complex organic
molecules.1
The development of ruthenium carbene com-
plexes (1 and 2 Figure 1) by Grubbs and co-workers is
particularly notable because of the remarkable functional
group tolerance, operational simplicity, high stability, and
availability.2
Although used extensively to form large-

  

Source: Andreana, Peter R. - Department of Chemistry, Wayne State University

 

Collections: Chemistry