title: Concise formal total synthesis of platensimycin mediated by a stereoselective autoxidation and hydroxyl group directed conjugative reduction.
abstract: The synthesis of 13, an advanced intermediate in the Nicolaou synthesis of platensimycin 1, was made from 9 by autoxidation to give 10, which was stereoselectively reduced providing 12. Finally, dehydration of 12 by heating in DMSO resulted in 13.
authors.affiliation: Department of Chemistry and Biochemistry, University of Texas at Austin, 1 University Station A5300, Austin, Texas 78712-1167, USA. p.magnus@mail.utexas.edu
authors.forename: Philip
authors.initials: P
authors.lastname: Magnus
authors.forename: Heriberto
authors.initials: H
authors.lastname: Rivera
authors.forename: Vince
authors.initials: V
authors.lastname: Lynch
mesh_terms: D000218:Adamantane / Q000138:chemical synthesis*; D000478:Alkylation; D062365:Aminobenzoates / Q000138:chemical synthesis*; D000813:Anilides / Q000138:chemical synthesis*; D017665:Hydroxyl Radical / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D010084:Oxidation-Reduction; D013237:Stereoisomerism
chemical_list: D062365:Aminobenzoates; D000813:Anilides; D017665:Hydroxyl Radical; D000218:Adamantane; C510909:platensimycin