title: Fluorous mixture synthesis of (-)-dictyostatin and three stereoisomers.
abstract: [reaction: see text] A mixture of four stereoisomers whose configurations are encoded by fluorous silyl protecting groups has been prepared and converted over 22 steps to a mixture of protected dictyostatins. Demixing by fluorous HPLC followed by removal of the fluorous protecting groups (detagging) provides dictyostatin and three C6,C7 stereoisomers. Biological evaluation showed that the monoepimers of the natural product retained highly potent activity.
authors.affiliation: Department of Chemistry, University of Pittsburgh, Pennsylvania 15260, USA.
authors.forename: Yoshikazu
authors.initials: Y
authors.lastname: Fukui
authors.forename: Arndt M
authors.initials: AM
authors.lastname: Brückner
authors.forename: Youseung
authors.initials: Y
authors.lastname: Shin
authors.forename: Raghavan
authors.initials: R
authors.lastname: Balachandran
authors.forename: Billy W
authors.initials: BW
authors.lastname: Day
authors.forename: Dennis P
authors.initials: DP
authors.lastname: Curran
mesh_terms: D005461:Fluorine / Q000737:chemistry*; D018942:Macrolides / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D018942:Macrolides; C470814:dictyostatin; D005461:Fluorine