First total synthesis of (+/-)-strychnofoline via a highly selective ring-expansion reaction.
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.
Lerchner
Andreas
A
Laboratorium für Organische Chemie, ETH-Zürich, CH-8093 Zürich, Switzerland.
Carreira
Erick M
EM
D000972:Antineoplastic Agents, Phytogenic / Q000138:chemical synthesis*; D026121:Indole Alkaloids / Q000138:chemical synthesis*; D007212:Indolizines / Q000138:chemical synthesis*; D031451:Strychnos / Q000737:chemistry
D000972:Antineoplastic Agents, Phytogenic; D026121:Indole Alkaloids; D007212:Indolizines; C471685:strychnofoline