title: Formal synthesis of (+/-)-platensimycin.
abstract: [reaction: see text] Reductive alkylation of 5-methoxy-1-tetralone (6) with 2,3-dibromopropene gave an equilibrium mixture of bicyclic diones 7 (51%) and 8 (35%). Radical cyclization of 7 afforded tricyclic dione 5 (84%), which was reduced, cyclized, and dehydrated to give tetracyclic alkene 13 in 63% yield. Allylic oxidation of 13 with SeO2 and activated MnO2 afforded enone 2 in 85% yield, thereby completing a short formal synthesis of (+/-)-platensimycin.
authors.affiliation: Department of Chemistry, MS 015, Brandeis University, Waltham, Massachusetts 02454-9110, USA.
authors.forename: Yefen
authors.initials: Y
authors.lastname: Zou
authors.forename: Chun-Hsing
authors.initials: CH
authors.lastname: Chen
authors.forename: Christopher D
authors.initials: CD
authors.lastname: Taylor
authors.forename: Bruce M
authors.initials: BM
authors.lastname: Foxman
authors.forename: Barry B
authors.initials: BB
authors.lastname: Snider
mesh_terms: D000218:Adamantane / Q000138:chemical synthesis* / Q000737:chemistry; D062365:Aminobenzoates / Q000138:chemical synthesis* / Q000737:chemistry; D000813:Anilides / Q000138:chemical synthesis* / Q000737:chemistry; D018360:Crystallography, X-Ray; D003500:Cyclization; D015394:Molecular Structure; D010084:Oxidation-Reduction; D014867:Water / Q000737:chemistry
chemical_list: D062365:Aminobenzoates; D000813:Anilides; D014867:Water; D000218:Adamantane; C510909:platensimycin