title: Final-stage Site-selective Acylation for the Total Synthesis of Natural Glycosides.
abstract: The first total syntheses of multifidosides A-C are reported. The prominent feature is an unconventional retrosynthesis based on organocatalytic site-selective acylation of unprotected glycosides at the final stage of synthesis. A notable advantage of this strategy is that it avoids the risks of undesired side reactions during the removal of the protecting groups at the final stage of total synthesis. The proposed synthetic strategy has another advantage in terms of efficient late-stage derivatization of natural products. Due to the predictability and reliability of the catalytic site-selective introduction of various functionalized acyl groups, the present synthetic strategy could provide a general synthetic route to 4-O-acylglycosides, such as phenylethanoid glycosides and ellagitannins, which are of biological interest.
authors.affiliation: Institute for Chemical Research, Kyoto University.
authors.forename: Yoshihiro
authors.initials: Y
authors.lastname: Ueda
mesh_terms: D000215:Acylation; D000970:Antineoplastic Agents / Q000138:chemical synthesis; D001688:Biological Products / Q000138:chemical synthesis*; D020134:Catalytic Domain; D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry; D008968:Molecular Conformation
chemical_list: D000970:Antineoplastic Agents; D001688:Biological Products; D006027:Glycosides