title: Efficient enantio- and diastereodivergent synthesis of poison-frog alkaloids 251O and trans-223B.
abstract: An efficient and flexible synthesis of poison-frog alkaloids 251O and trans-223B has been achieved by using for both alkaloids an enantiodivergent process starting from the common lactam 1. The relative stereochemistry of 251O and trans-223B was determined to be 7 (R = n-C(7)H(15), R' = n-Pr) and 14 by the present enantioselective synthesis.
authors.affiliation: Graduate School of Medicine and Pharmaceutical Sciences, University of Toyama, Sugitani 2630, Toyama 930-0194, Japan. toyooka@pha.u-toyama.ac.jp
authors.forename: Naoki
authors.initials: N
authors.lastname: Toyooka
authors.forename: Dejun
authors.initials: D
authors.lastname: Zhou
authors.forename: Hideo
authors.initials: H
authors.lastname: Nemoto
authors.forename: Yasuhiro
authors.initials: Y
authors.lastname: Tezuka
authors.forename: Shigetoshi
authors.initials: S
authors.lastname: Kadota
authors.forename: Nirina R
authors.initials: NR
authors.lastname: Andriamaharavo
authors.forename: H Martin
authors.initials: HM
authors.lastname: Garraffo
authors.forename: Thomas F
authors.initials: TF
authors.lastname: Spande
authors.forename: John W
authors.initials: JW
authors.lastname: Daly
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D000475:Alkenes / Q000737:chemistry; D000818:Animals; D002625:Chemistry, Organic / Q000379:methods*; D002849:Chromatography, Gas / Q000379:methods; D015195:Drug Design; D007700:Kinetics; D008956:Models, Chemical; D011042:Poisons / Q000737:chemistry; D011758:Pyrroles / Q000737:chemistry; D011763:Pyrrolizidine Alkaloids / Q000737:chemistry*; D011898:Ranidae; D017550:Spectroscopy, Fourier Transform Infrared / Q000379:methods; D013237:Stereoisomerism
chemical_list: D000470:Alkaloids; D000475:Alkenes; D011042:Poisons; D011758:Pyrroles; D011763:Pyrrolizidine Alkaloids; C545571:xenovenine