title: A Formal Total Synthesis of (±)-Kopsihainanine A Using a Raney-Cobalt Mediated Reductive Cyclization Route to Polyhydroquinolines.
abstract: Perhydroquinoline 4, the product of a Raney-cobalt mediated reductive cyclization reaction, was readily converted into the cis-ring-fused perhydroquinoline 15 that could be epimerized to its trans-fused counterpart 2 on sequential treatment with iodosylbenzene then sodium borohydride. Tetracycle 2 is an advanced intermediate associated with a recently reported total synthesis of the alkaloid kopsihainanine A (1).
authors.affiliation: Research School of Chemistry, Institute of Advanced Studies, The Australian National University , Canberra, ACT 2601, Australia.
authors.forename: Shen H
authors.initials: SH
authors.lastname: Tan
authors.affiliation: Research School of Chemistry, Institute of Advanced Studies, The Australian National University , Canberra, ACT 2601, Australia.
authors.forename: Martin G
authors.initials: MG
authors.lastname: Banwell
authors.affiliation: Research School of Chemistry, Institute of Advanced Studies, The Australian National University , Canberra, ACT 2601, Australia.
authors.forename: Anthony C
authors.initials: AC
authors.lastname: Willis
mesh_terms: D003035:Cobalt / Q000737:chemistry*; D003500:Cyclization; D006576:Heterocyclic Compounds, 4 or More Rings / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy / Q000379:methods; D010084:Oxidation-Reduction; D015363:Quinolones / Q000737:chemistry*; D021241:Spectrometry, Mass, Electrospray Ionization
chemical_list: D006576:Heterocyclic Compounds, 4 or More Rings; D015363:Quinolones; C562138:kopsihainanine A; D003035:Cobalt