title: Cross-coupling reaction of saccharide-based alkenyl boronic acids with aryl halides: the synthesis of bergenin.
abstract: A convenient synthetic pathway enabling D-glucal and D-galactal pinacol boronates to be prepared in good isolated yields was achieved. Both pinacol boronates were tested in a series of cross-coupling reactions under Suzuki-Miyaura cross-coupling conditions to obtain the corresponding aryl, heteroaryl, and alkenyl derivatives in high isolated yields. This methodology was applied to the formal synthesis of the glucopyranoside moiety of papulacandin D and the first total synthesis of bergenin.
authors.affiliation: Department of Chemistry of Natural Compounds, Institute of Chemical Technology, Technická 5, 166 28 Praha 6 (Czech Republic), Fax: (+420) 220444422. parkank@vscht.cz.
authors.forename: Kamil
authors.initials: K
authors.lastname: Parkan
authors.forename: Radek
authors.initials: R
authors.lastname: Pohl
authors.forename: Martin
authors.initials: M
authors.lastname: Kotora
mesh_terms: D000617:Aminoglycosides / Q000138:chemical synthesis / Q000737:chemistry; D001578:Benzopyrans / Q000138:chemical synthesis* / Q000737:chemistry; D001897:Boronic Acids / Q000138:chemical synthesis / Q000737:chemistry*; D054714:Echinocandins / Q000138:chemical synthesis / Q000737:chemistry; D005690:Galactose / Q000031:analogs & derivatives / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000617:Aminoglycosides; D001578:Benzopyrans; D001897:Boronic Acids; D054714:Echinocandins; C002038:galactal; C014732:papulacandins; C006741:bergenin; D005690:Galactose
keywords: CC coupling; glycosides; natural products; protecting groups; synthetic methods