title: Efficient synthesis of lupane-type saponins via gold(I)-catalyzed glycosylation with glycosyl ortho-alkynylbenzoates as donors.
abstract: Glycosylation of the acid labile betulin and betulinic acid derivatives was achieved with glycosyl ortho-hexynylbenzoates as donors under the catalysis of PPh(3)AuNTf(2); this enabled the efficient synthesis of lupane-type saponins, as exemplified by the total synthesis of the proposed betulinic acid trisaccharide from Bersama engleriana.
authors.affiliation: State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China.
authors.forename: Yan
authors.initials: Y
authors.lastname: Li
authors.forename: Jiansong
authors.initials: J
authors.lastname: Sun
authors.forename: Biao
authors.initials: B
authors.lastname: Yu
mesh_terms: D001565:Benzoates / Q000737:chemistry*; D002384:Catalysis; D006031:Glycosylation; D006046:Gold / Q000737:chemistry*; D019684:Magnoliopsida / Q000737:chemistry; D015394:Molecular Structure; D053978:Pentacyclic Triterpenes; D012503:Saponins / Q000138:chemical synthesis* / Q000737:chemistry; D014312:Trisaccharides / Q000138:chemical synthesis* / Q000737:chemistry; D014315:Triterpenes / Q000138:chemical synthesis* / Q000737:chemistry*; D000094062:Betulinic Acid
chemical_list: D001565:Benzoates; D053978:Pentacyclic Triterpenes; D012503:Saponins; D014312:Trisaccharides; D014315:Triterpenes; C480546:lupane; D006046:Gold; D000094062:Betulinic Acid