title: Regiospecific and stereoselective syntheses of (+/-) morphine, codeine, and thebaine via a highly stereocontrolled intramolecular 4 + 2 cycloaddition leading to a phenanthrofuran system.
abstract: Total syntheses of the morphine alkaloids are described that use a direct stereoselective formation of the phenanthrofuran system via an intramolecular 4 + 2 cycloaddition of a diene tethered to the 4-position of a 7-methoxybenzofuran-3-carboxylic acid ester.
authors.affiliation: Department of Chemistry, Columbia University, New York, New York, USA. gjs8@columbia.edu
authors.forename: Gilbert
authors.initials: G
authors.lastname: Stork
authors.forename: Ayako
authors.initials: A
authors.lastname: Yamashita
authors.forename: Julian
authors.initials: J
authors.lastname: Adams
authors.forename: Gary R
authors.initials: GR
authors.lastname: Schulte
authors.forename: Richard
authors.initials: R
authors.lastname: Chesworth
authors.forename: Yoji
authors.initials: Y
authors.lastname: Miyazaki
authors.forename: Jay J
authors.initials: JJ
authors.lastname: Farmer
mesh_terms: D003061:Codeine / Q000138:chemical synthesis*; D015394:Molecular Structure; D009020:Morphine / Q000138:chemical synthesis*; D013237:Stereoisomerism; D013797:Thebaine / Q000138:chemical synthesis*
chemical_list: D013797:Thebaine; D009020:Morphine; D003061:Codeine