title: Stereodivergent resolution of oxabicyclic ketones: preparation of key intermediates for platensimycin and other natural products.
abstract: An improved methodology for the preparation of enantiopure oxabicyclo[3.2.1]octadienes via a stereodivergent resolution is reported. High catalyst control proximal to the oxabridged stereocenter produces readily separable diastereomers in high yield (>92%) and with excellent optical purity (>95% ee). This resolution strategy is amenable to large-scale preparations, and the utility of the resolution was further demonstrated in the asymmetric preparation of a key intermediate used in the synthesis of the antibiotic (-)-platensimycin.
authors.affiliation: Department of Pharmaceutical Sciences, University of Connecticut , 69 North Eagleville Road, Storrs, Connecticut 06269, United States.
authors.forename: Michael D
authors.initials: MD
authors.lastname: VanHeyst
authors.forename: E Zachary
authors.initials: EZ
authors.lastname: Oblak
authors.forename: Dennis L
authors.initials: DL
authors.lastname: Wright
mesh_terms: D000218:Adamantane / Q000138:chemical synthesis* / Q000737:chemistry; D062365:Aminobenzoates / Q000138:chemical synthesis* / Q000737:chemistry; D000813:Anilides / Q000138:chemical synthesis* / Q000737:chemistry; D001688:Biological Products / Q000737:chemistry*; D001643:Bridged Bicyclo Compounds / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D062365:Aminobenzoates; D000813:Anilides; D001688:Biological Products; D001643:Bridged Bicyclo Compounds; D007659:Ketones; D000218:Adamantane; C510909:platensimycin