title: Enantioselective synthesis of (+)- and (-)-dihydroepiepoformin and (+)-epiepoformin.
abstract: [reaction: see text] The enantioselective synthesis of both enantiomers of dihydroepiepoformin (1) and (+)-epiepoformin (2) was achieved from (p-tolylsulfinyl)methyl-p-quinols (SR)- or (SS)-3 and (4R,SR)-4, respectively. Key features include the stereocontrolled conjugate addition of AlMe3 to p-quinol 3 and retrocondensation to the ketone functionality, previous to oxidation of the beta-hydroxy sulfoxide moiety of advanced intermediates to the corresponding sulfone.
authors.affiliation: Departamento de Química Orgánica (C-I), Universidad Autónoma de Madrid, Cantoblanco, 28049 Madrid, Spain. carmen.carrenno@uam.es
authors.forename: M Carmen
authors.initials: MC
authors.lastname: Carreño
authors.forename: Estíbaliz
authors.initials: E
authors.lastname: Merino
authors.forename: María
authors.initials: M
authors.lastname: Ribagorda
authors.forename: Alvaro
authors.initials: A
authors.lastname: Somoza
authors.forename: Antonio
authors.initials: A
authors.lastname: Urbano
mesh_terms: D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000138:chemical synthesis*; D002384:Catalysis; D006873:Hydroquinones / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry*; D015394:Molecular Structure; D010084:Oxidation-Reduction; D010407:Penicillium / Q000737:chemistry; D013237:Stereoisomerism; D013454:Sulfoxides / Q000737:chemistry*
chemical_list: D019086:Bridged Bicyclo Compounds, Heterocyclic; D006873:Hydroquinones; D007659:Ketones; D013454:Sulfoxides; C096606:dihydroepiepoformin; C506854:epiepoformin