title: A multifaceted phosphate tether: application to the C15-C30 subunit of dolabelides A-D.
abstract: Construction of the C15-C30 subunit of dolabelide utilizing a temporary phosphate tether is described. Two routes are reported that make use of the orthogonal protecting- and leaving-group properties innate to phosphate esters. One route relies on a selective terminal oxidation, while a second utilizes a CM/selective hydrogenation sequence. Both routes depend on a highly regio- and diastereoselective cuprate addition to set the requisite stereochemistry at C22.
authors.affiliation: Department of Chemistry, University of Kansas, 1251 Wescoe Hall Drive, Lawrence, Kansas 66045, USA.
authors.forename: Alan
authors.initials: A
authors.lastname: Whitehead
authors.forename: Joshua D
authors.initials: JD
authors.lastname: Waetzig
authors.forename: Christopher D
authors.initials: CD
authors.lastname: Thomas
authors.forename: Paul R
authors.initials: PR
authors.lastname: Hanson
mesh_terms: D002384:Catalysis; D018942:Macrolides / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009943:Organophosphorus Compounds / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D018942:Macrolides; D009943:Organophosphorus Compounds; C481199:dolabelide A; C481200:dolabelide B; C524147:dolabelide C; C509949:dolabelide D