title: Palladium-catalyzed potassium enoxyborate alkylation of enantiopure Hajos-Parrish indenone to construct rearranged steroid ring systems.
abstract: Here we report the stereo- and regiospecific C-6 alkylation of a trans-inden-5-one (from optically pure Hajos-Parrish ketone) with allylic electrophiles. Use of this alkylation procedure has led to an improved synthesis of the benz[f]indene ring system and the first enantiospecific total syntheses of the cyclopenta[b]anthracene and cyclopenta[b]phenanthrene ring systems (two synthetic routes).
authors.affiliation: Department of Molecular Biology and Pharmacology, Washington University School of Medicine, St. Louis, Missouri 63110, USA.
authors.forename: Izabella
authors.initials: I
authors.lastname: Jastrzebska
authors.forename: Jamie B
authors.initials: JB
authors.lastname: Scaglione
authors.forename: Gregory T
authors.initials: GT
authors.lastname: Dekoster
authors.forename: Nigam P
authors.initials: NP
authors.lastname: Rath
authors.forename: Douglas F
authors.initials: DF
authors.lastname: Covey
mesh_terms: D000478:Alkylation; D000873:Anthracenes / Q000737:chemistry; D001554:Benzene / Q000737:chemistry; D001881:Borates / Q000737:chemistry*; D002384:Catalysis; D007192:Indenes / Q000737:chemistry*; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*; D013256:Steroids / Q000737:chemistry*
chemical_list: D000873:Anthracenes; D001881:Borates; D007192:Indenes; D013256:Steroids; D010165:Palladium; C034020:anthracene; D001554:Benzene