Synthesis of (+/-)-strychnofoline via a highly convergent selective annulation reaction.
Studies aimed at preparing (+/-)-strychnofoline by total synthesis are detailed. The route described makes use of a recently developed MgI(2)-mediated ring-expansion reaction of spiro[cyclopropan-1,3'-oxindole] with a cyclic disubstituted aldimine. The ring-expansion product was formed as a single diastereoisomer in 55 % yield, possessing the same stereochemical pattern found in strychnofoline. In addition, our synthetic effort has led to the development of new reaction methodology to access 3,4-disubstituted cyclic aldimines.
Lerchner
Andreas
A
Laboratorium für Organische Chemie, ETH Zürich, HCI H335, 8093 Zürich, Switzerland.
Carreira
Erick M
EM
D000972:Antineoplastic Agents, Phytogenic / Q000138:chemical synthesis*; D003500:Cyclization; D026121:Indole Alkaloids / Q000138:chemical synthesis*; D007212:Indolizines / Q000138:chemical synthesis*; D008956:Models, Chemical; D013141:Spiro Compounds / Q000138:chemical synthesis*; D013237:Stereoisomerism
D000972:Antineoplastic Agents, Phytogenic; D026121:Indole Alkaloids; D007212:Indolizines; D013141:Spiro Compounds; C471685:strychnofoline