title: Toward a structure-activity relationship for apoptolidin: selective functionalization of the hydroxyl group array.
abstract: [reaction: see text] To investigate the structural basis for the exceptional selectivity and activity of apoptolidin (1), a strategy has been devised that allows for selective functionalization of seven of its eight hydroxyl groups based on progressive silyl protection, derivatization, and deprotection. The syntheses of these derivatives and their ability to inhibit F(0)F(1)-ATPase are reported.
authors.affiliation: Department of Chemistry, Stanford University, Stanford, California, 94305-5080, USA. wenderp@stanford.edu
authors.forename: Paul A
authors.initials: PA
authors.lastname: Wender
authors.forename: Orion D
authors.initials: OD
authors.lastname: Jankowski
authors.forename: Elie A
authors.initials: EA
authors.lastname: Tabet
authors.forename: Haruo
authors.initials: H
authors.lastname: Seto
mesh_terms: D000818:Animals; D000900:Anti-Bacterial Agents / Q000737:chemistry* / Q000494:pharmacology*; D006801:Humans; D006900:Hydroxylation; D020128:Inhibitory Concentration 50; D018942:Macrolides; D024101:Mitochondrial Proteins; D006180:Proton-Translocating ATPases / Q000037:antagonists & inhibitors; D013329:Structure-Activity Relationship
chemical_list: D000900:Anti-Bacterial Agents; D018942:Macrolides; D024101:Mitochondrial Proteins; D006180:Proton-Translocating ATPases; C114125:apoptolidin