Synthesis of 2,6-dideoxysugars via ring-closing olefinic metathesis.
[formula: see text] Grubbs' RuCl2 (=CHPh)(PCy3)2 (catalyst 1) and RuCl2(=CHPh)(PCy3)(IMess) (catalyst 2) complexes have been successfully utilized in the construction of beta,gamma-unsaturated delta-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.
Andreana
Peter R
PR
Department of Chemistry, Wayne State University, Detroit, Michigan, USA.
McLellan
Jason S
JS
Chen
Yongchen
Y
Wang
Peng George
PG
D000475:Alkenes / Q000737:chemistry; D003500:Cyclization; D007783:Lactones / Q000737:chemistry; D009005:Monosaccharides / Q000138:chemical synthesis*; D013237:Stereoisomerism
D000475:Alkenes; D007783:Lactones; D009005:Monosaccharides