title: A solution- and solid-phase approach to tetrahydroquinoline-derived polycyclics having a 10-membered ring.
abstract: With the goal of library generation using a polycyclic derivative 5 having an enamide functional group, a simple and practical, enantioselective synthesis of tetrahydroquinoline derivative 2 was achieved. The phenolic hydroxyl group in compound 2 was utilized as an anchoring site for solid-phase synthesis. The ring closing metathesis approach yielded the desired polycyclic product 5 on solid phase in five steps (overall 40% yield). Compound 5 is a novel scaffold for the library generation of natural product-like polycyclics having a functionalized medium ring for obtaining a new class of small molecules to be utilized as chemical probes.
authors.affiliation: Department of Chemistry, University of Ottawa, 10 Marie Curie, Ottawa, Canada K1N 6N5.
authors.forename: Shahriar
authors.initials: S
authors.lastname: Khadem
authors.forename: Reni
authors.initials: R
authors.lastname: Joseph
authors.forename: Majid
authors.initials: M
authors.lastname: Rastegar
authors.forename: Donald M
authors.initials: DM
authors.lastname: Leek
authors.forename: Kostantin A
authors.initials: KA
authors.lastname: Oudatchin
authors.forename: Prabhat
authors.initials: P
authors.lastname: Arya