De novo asymmetric synthesis of an alpha-6-deoxyaltropyranoside as well as its 2-/3-deoxy and 2,3-dideoxy congeners.
A highly divergent de novo asymmetric synthesis of benzyl alpha-6-deoxyaltropyranoside, benzyl alpha-ascarylopyranoside, benzyl alpha-amicetopyranoside, and benzyl alpha-digitoxopyranoside has been achieved via a common pyranone intermediate. The routes rely upon a palladium(0)-catalyzed glycosylation reaction and corresponding post-glycosylation transformations. The control of the absolute and relative stereochemical configuration came from a Noyori reduction of 2-acylfuran and subsequent diastereoselective introduction of other stereogenic centers.
Shan
Mingde
M
Department of Chemistry, West Virginia University, Morgantown, West Virginia 26506, USA.
Xing
Yalan
Y
O'Doherty
George A
GA
D002384:Catalysis; D005663:Furans / Q000737:chemistry; D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry*; D006031:Glycosylation; D006601:Hexoses / Q000737:chemistry; D010165:Palladium / Q000737:chemistry; D013237:Stereoisomerism
D005663:Furans; D006027:Glycosides; D006601:Hexoses; D010165:Palladium