title: Highly stereocontrolled and regiocontrolled syntheses of 2,3,4-trisubstituted alkanoates and lactones.
abstract: New chlorodiols (±)-3 and (±)-5 are densely functionalized and versatile synthons. They are converted in one step on a gram scale into 2-chlorolactones (±)-6 and (±)-7 and into 4-hydroxy glycidate esters (±)-9 and (±)-10. The 4-hydroxy glycidate esters (±)-9 and (±)-10 are converted stereospecifically and regiospecifically into oxazolines (±)-13 and (±)-14 and into cyclic carbamates (±)-18-(±)-20. The 4-hydroxy glycidate ester (±)-10 undergoes stereocontrolled and regiocontrolled epoxide opening by sodium azide to form the 2-azido-3,4-dihydroxy alkanoate (±)-21. Finally, chlorodiol (±)-5 reacts stereospecifically with silver triflate to form the 2,3-dihydroxyfuranone (±)-26.
authors.affiliation: Department of Chemistry, The Johns Hopkins University, 3400 North Charles Street, Baltimore, Maryland 21218, USA.
authors.forename: Christopher P
authors.initials: CP
authors.lastname: Hencken
authors.forename: Douglas T
authors.initials: DT
authors.lastname: Genna
authors.forename: Maxime A
authors.initials: MA
authors.lastname: Siegler
authors.forename: Gary H
authors.initials: GH
authors.lastname: Posner