title: A total synthesis of (-)-Hortonone C.
abstract: A total synthesis of the cytotoxic terpenoid hortonone C was accomplished and its absolute stereochemistry confirmed. Intermediate (+)-4was synthesized using either an asymmetric conjugate addition strategy, or by elaboration of the Hajos-Parrish ketone. Reduction of (+)-4under dissolving-metal conditions and trapping the enolate intermediate served to control the cis-stereochemistry at the ring fusion and provide a silyl enol ether necessary for ring expansion. Comparison of optical rotation data confirmed that the absolute configuration of natural hortonone C is (6S,7S,10S).
authors.affiliation: Department of Chemistry, New Mexico Institute of Mining and Technology, Socorro NM 87801, United States.
authors.forename: Doleshwar
authors.initials: D
authors.lastname: Niroula
authors.affiliation: Department of Chemistry, New Mexico Institute of Mining and Technology, Socorro NM 87801, United States; Department of Biology, New Mexico Institute of Mining and Technology, Socorro NM 87801, United States.
authors.forename: Liam P
authors.initials: LP
authors.lastname: Hallada
authors.affiliation: Department of Biology, New Mexico Institute of Mining and Technology, Socorro NM 87801, United States.
authors.forename: Snezna
authors.initials: S
authors.lastname: Rogelj
authors.affiliation: Department of Chemistry, New Mexico Institute of Mining and Technology, Socorro NM 87801, United States.
authors.forename: Rodolfo
authors.initials: R
authors.lastname: Tello-Aburto
keywords: Asymmetric Conjugate Addition; Hortonones; Hydroazulene; Hydroindane; Natural Products; Total Synthesis