title: First total synthesis of (+/-)-strychnofoline via a highly selective ring-expansion reaction.
abstract: An efficient synthesis of the antitumor alkaloid (+/-)-strychnofoline is documented. Key to the development of the highly convergent strategy delineated is the coupling of a cyclic imine with spiro[cyclopropan-1,3'-oxindole], which takes place in a highly diastereoselective manner. The ability to conduct annulation reactions of spirocyclopropyloxindoles with functionalized cyclic imines provides new avenues for the preparation of this important class of biologically active structures.
authors.affiliation: Laboratorium für Organische Chemie, ETH-Zürich, CH-8093 Zürich, Switzerland.
authors.forename: Andreas
authors.initials: A
authors.lastname: Lerchner
authors.forename: Erick M
authors.initials: EM
authors.lastname: Carreira
mesh_terms: D000972:Antineoplastic Agents, Phytogenic / Q000138:chemical synthesis*; D026121:Indole Alkaloids / Q000138:chemical synthesis*; D007212:Indolizines / Q000138:chemical synthesis*; D031451:Strychnos / Q000737:chemistry
chemical_list: D000972:Antineoplastic Agents, Phytogenic; D026121:Indole Alkaloids; D007212:Indolizines; C471685:strychnofoline