De novo synthesis of the trisaccharide subunit of landomycins A and E.
A highly enantio- and diastereoselective synthesis of alpha- -rhodinose, beta-d-olivose as well as the trisaccharide portion of landomycin A from achiral acetyl furan has been developed. The key transformations include the palladium-catalyzed glycosylation, Myers' reductive rearrangement, diastereoselective dihydroxylation, and regioselective Mitsunobu inversion. A Mitsunobu reaction on a six member ring cis-1,2-diol was found to chemoselectively discriminate between equatorial and axial alcohols and to stereoselectively convert cis-1,2-diol into anti-1,2-diol.
Zhou
Maoquan
M
Department of Chemistry, West Virginia University, Morgantown, West Virginia 26506, USA.
O'Doherty
George A
GA
D000617:Aminoglycosides / Q000737:chemistry*; D013237:Stereoisomerism; D013379:Substrate Specificity; D014312:Trisaccharides / Q000138:chemical synthesis* / Q000737:chemistry
D000617:Aminoglycosides; D014312:Trisaccharides; C113593:landomycin E; C064648:landomycin A