title: Mechanistic study of the spiroindolones: a new class of antimalarials.
abstract: During the synthesis of the new antimalarial drug candidate NITD609, a high degree of diastereoselectivity was observed in the Pictet-Spengler reaction. By isolating both the 4E and 4Z imine intermediates, a systematic mechanistic study of the reaction under both kinetic and thermodynamic conditions was conducted. This study provides insight into the source of the diastereoselectivity for this important class of compounds.
authors.affiliation: Novartis Institute for Tropical Diseases, 10 Biopolis Road, #05-01 Chromos, Singapore. bin.zou@novartis.com
authors.forename: Bin
authors.initials: B
authors.lastname: Zou
authors.forename: Peiling
authors.initials: P
authors.lastname: Yap
authors.forename: Louis-Sebastian
authors.initials: LS
authors.lastname: Sonntag
authors.forename: Seh Yong
authors.initials: SY
authors.lastname: Leong
authors.forename: Bryan K S
authors.initials: BK
authors.lastname: Yeung
authors.forename: Thomas H
authors.initials: TH
authors.lastname: Keller
mesh_terms: D000962:Antimalarials / Q000138:chemical synthesis / Q000737:chemistry*; D055808:Drug Discovery; D007211:Indoles / Q000138:chemical synthesis / Q000737:chemistry*; D007700:Kinetics; D015394:Molecular Structure; D013141:Spiro Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000962:Antimalarials; D007211:Indoles; C552304:NITD 609; D013141:Spiro Compounds