title: Synthetic studies toward phorboxazole A. stereoselective synthesis of the C(28)-C(46) side chain fragment.
abstract: A stereoselective synthesis of the C(28)-C(46) fragment (3) of phorboxazole A is described. Key advances include an enantioselective allylation to establish the stereochemistry of the tetrahydropyran unit and a useful SmI(2)-mediated modification of the Barbier reaction of iodomethyloxazole 15 with aldehyde 14.
authors.affiliation: Department of Chemistry, Indiana University, 800 East Kirkwood Avenue, Bloomington, Indiana 47405-7102, USA. williamd@indiana.edu
authors.forename: D R
authors.initials: DR
authors.lastname: Williams
authors.forename: M P
authors.initials: MP
authors.lastname: Clark
authors.forename: U
authors.initials: U
authors.lastname: Emde
authors.forename: M A
authors.initials: MA
authors.lastname: Berliner
mesh_terms: D000818:Animals; D000970:Antineoplastic Agents / Q000138:chemical synthesis*; D006576:Heterocyclic Compounds, 4 or More Rings / Q000138:chemical synthesis*; D010080:Oxazoles / Q000138:chemical synthesis*; D011161:Porifera / Q000737:chemistry; D011714:Pyrans / Q000138:chemical synthesis; D013237:Stereoisomerism
chemical_list: D000970:Antineoplastic Agents; D006576:Heterocyclic Compounds, 4 or More Rings; D010080:Oxazoles; D011714:Pyrans; C408887:phorboxazole A