title: First synthesis of enantiopure 1,6-difunctionalized dodecahydrobenz[f]indenes.
abstract: An enantiospecific route to the previously unreported 1,6-difunctionalized dodecahydrobenz[f]indene ring system is described. Optically pure Hajos-Parrish ketone is used as the building block for preparation of a 6-methyleneinden-5-ol. This allylic alcohol is then utilized in a Claisen rearrangement under Johnson's conditions to introduce a side chain that is further modified and cyclized to produce the benz[f]indene ring system.
authors.affiliation: Department of Molecular Biology and Pharmacology, Washington University School of Medicine, 660 South Euclid Avenue, St. Louis, MI 63110, USA.
authors.forename: Jamie B
authors.initials: JB
authors.lastname: Scaglione
authors.forename: Nigam P
authors.initials: NP
authors.lastname: Rath
authors.forename: Douglas F
authors.initials: DF
authors.lastname: Covey
mesh_terms: D018682:GABA Agents / Q000138:chemical synthesis* / Q000737:chemistry; D007192:Indenes / Q000138:chemical synthesis*; D013237:Stereoisomerism; D013256:Steroids / Q000737:chemistry; D013329:Structure-Activity Relationship
chemical_list: D018682:GABA Agents; D007192:Indenes; D013256:Steroids