Efficient total syntheses and structural verification of both diospongins A and B via a common delta-lactone intermediate.
The total syntheses of the two aryl C-glycoside natural products diospongins A and B are described. The key reactions involved stereoselective reductions of the appropriate oxocarbenium cations that were derived from a common delta-lactone intermediate.
Sawant
Kailas B
KB
Department of Chemistry, The University of Alabama, Tuscaloosa, Alabama 35487-0336, USA.
Jennings
Michael P
MP
D001688:Biological Products / Q000138:chemical synthesis; D006027:Glycosides; D007783:Lactones / Q000737:chemistry; D009005:Monosaccharides / Q000138:chemical synthesis*; D010084:Oxidation-Reduction; D011714:Pyrans / Q000138:chemical synthesis*; D013237:Stereoisomerism
D001688:Biological Products; C438934:C-glycoside; D006027:Glycosides; D007783:Lactones; D009005:Monosaccharides; D011714:Pyrans; C521317:diospongin A; C521318:diospongin B