title: A practical asymmetric synthesis of trans-4,5-benzhydrindan-1-ones as a precursor of A-nor B-aromatic steroidal compounds.
abstract: The enantio-controlled synthesis of trans-4,5-benzhydrindan-1-ones was achieved by means of a stereoselective [4+2] cycloaddition of o-quinodimethanes generated by a thermal cleavage of benzocyclobutene derivatives as a key step. The chiral substrates of the thermal reaction were synthesized by a diastereoselective Grignard addition to the chiral O-isopropylideneglyceroketones connected to a benzocyclobutene ring, which were simply prepared from D-mannitol as a chiral source. This approach can provide a new efficient access to A-nor B-aromatic steroidal compounds.
authors.affiliation: Faculty of Pharmaceutical Sciences, Toyama Medical and Pharmaceutical University, 2630 Sugitani, Toyama 930-0194, Japan.
authors.forename: Yuji
authors.initials: Y
authors.lastname: Matsuya
authors.forename: Seiji
authors.initials: S
authors.lastname: Masuda
authors.forename: Takakatsu
authors.initials: T
authors.lastname: Itoh
authors.forename: Taiki
authors.initials: T
authors.lastname: Murai
authors.forename: Hideo
authors.initials: H
authors.lastname: Nemoto
mesh_terms: D001555:Benzene Derivatives / Q000138:chemical synthesis*; D013237:Stereoisomerism; D013256:Steroids / Q000737:chemistry*
chemical_list: D001555:Benzene Derivatives; D013256:Steroids