title: Synthesis of Ocotillol-Type Ginsenosides.
abstract: A total of 14 ocotillol-type ginsenosides were conveniently synthesized employing glycosylation of ocotillol sapogenin derivatives with glucosyl ortho-alkynylbenzoate donors under the promotion of a gold(I) catalyst as the key step. Relying on a rational protecting group strategy and the unexpected regioselectivity of the glycosylation of the 3,25-diol sapogenins (2a/2b, 5a/5b) for the tertiary 25-OH, mono 3-O-glucosyl ocotillol-PPD, 6-O-glucosyl ocotillol-PPT, 25-O-glucosyl ocotillol-PPD/PPT and 3,25-di-O-glucosyl ocotillol-PPD/PPT ginsenosides were prepared in which the configuration at the C-24 is either R or S.
authors.affiliation: State Key Laboratory of Bio-organic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences , 345 Lingling Road, Shanghai 200032, China.
authors.forename: Renzeng
authors.initials: R
authors.lastname: Shen
authors.affiliation: State Key Laboratory of Bio-organic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences , 345 Lingling Road, Shanghai 200032, China.
authors.forename: Xin
authors.initials: X
authors.lastname: Cao
authors.affiliation: State Key Laboratory of Bio-organic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences , 345 Lingling Road, Shanghai 200032, China.
authors.forename: Stephane
authors.initials: S
authors.lastname: Laval
authors.affiliation: National Research Center for Carbohydrate Synthesis, Jiangxi Normal University , 437 West Beijing Road, Nanchang, 330027, China.
authors.forename: Jiansong
authors.initials: J
authors.lastname: Sun
authors.affiliation: State Key Laboratory of Bio-organic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences , 345 Lingling Road, Shanghai 200032, China.
authors.forename: Biao
authors.initials: B
authors.lastname: Yu
mesh_terms: D018360:Crystallography, X-Ray; D036145:Ginsenosides / Q000138:chemical synthesis* / Q000737:chemistry; D006031:Glycosylation; D015394:Molecular Structure; D013057:Spectrum Analysis / Q000379:methods
chemical_list: D036145:Ginsenosides; C524540:ocotillol