Convergent C-glycolipid synthesis via the Ramberg-Bäcklund reaction: active antiproliferative glycolipids.
[formula: see text] A novel methodology has been developed, employing the Ramberg-Bäcklund rearrangement and ionic hydrogenation to synthesize C-glycosides with high stereoselectivity at the anomeric center. The C-glycolipid 14b exhibits antiproliferative properties similar to those of O-glycoside analogue 14a.
Yang
G
G
Department of Chemistry, Hunter College/CUNY, New York 10021, USA.
Franck
R W
RW
Byun
H S
HS
Bittman
R
R
Samadder
P
P
Arthur
G
G
D000970:Antineoplastic Agents / Q000138:chemical synthesis*; D004354:Drug Screening Assays, Antitumor; D006017:Glycolipids / Q000138:chemical synthesis*; D006801:Humans; D008968:Molecular Conformation; D013237:Stereoisomerism; D014407:Tumor Cells, Cultured
D000970:Antineoplastic Agents; D006017:Glycolipids