title: Stereoselective Total Synthesis of (-)-Renieramycin T.
abstract: A stereoselective total synthesis of (-)-Renieramycin T (1t) from a key tetrahydroisoquinoline intermediate previously utilized in our formal total synthesis of Ecteinascidin 743 is described. The synthesis features a concise approach for construction of the pentacyclic framework using a Pictet-Spengler cyclization of bromo-substituted carbinolamine 17, which obviates the regioselectivity problem of the Pictet-Spengler cyclization. The results of cytotoxicity studies are also presented.
authors.affiliation: Graduate School of Pharmaceutical Sciences, Meiji Pharmaceutical University , 2-522-1 Noshio, Kiyose, Tokyo 204-8588, Japan.
authors.forename: Masashi
authors.initials: M
authors.lastname: Yokoya
authors.affiliation: Graduate School of Pharmaceutical Sciences, Meiji Pharmaceutical University , 2-522-1 Noshio, Kiyose, Tokyo 204-8588, Japan.
authors.forename: Ryoko
authors.initials: R
authors.lastname: Toyoshima
authors.affiliation: Graduate School of Pharmaceutical Sciences, Meiji Pharmaceutical University , 2-522-1 Noshio, Kiyose, Tokyo 204-8588, Japan.
authors.forename: Toshihiro
authors.initials: T
authors.lastname: Suzuki
authors.affiliation: Department of Chemistry, Colorado State University , Fort Collins, Colorado 80523, United States.|The University of Colorado Cancer Center , Aurora, Colorado 80045, United States.
authors.forename: Vy H
authors.initials: VH
authors.lastname: Le
authors.affiliation: Department of Chemistry, Colorado State University , Fort Collins, Colorado 80523, United States.|The University of Colorado Cancer Center , Aurora, Colorado 80045, United States.
authors.forename: Robert M
authors.initials: RM
authors.lastname: Williams
authors.affiliation: Graduate School of Pharmaceutical Sciences, Meiji Pharmaceutical University , 2-522-1 Noshio, Kiyose, Tokyo 204-8588, Japan.
authors.forename: Naoki
authors.initials: N
authors.lastname: Saito
mesh_terms: D003500:Cyclization; D006863:Hydrogen-Ion Concentration; D009682:Magnetic Resonance Spectroscopy; D013237:Stereoisomerism; D044005:Tetrahydroisoquinolines / Q000138:chemical synthesis*
chemical_list: D044005:Tetrahydroisoquinolines; C000627233:renieramycin T