Synthetic studies toward phorboxazole A. stereoselective synthesis of the C(28)-C(46) side chain fragment.
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.
Williams
D R
DR
Department of Chemistry, Indiana University, 800 East Kirkwood Avenue, Bloomington, Indiana 47405-7102, USA. williamd@indiana.edu
Clark
M P
MP
Emde
U
U
Berliner
M A
MA
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
D000970:Antineoplastic Agents; D006576:Heterocyclic Compounds, 4 or More Rings; D010080:Oxazoles; D011714:Pyrans; C408887:phorboxazole A