Nine-step enantioselective total synthesis of (+)-minfiensine.
An enantioselective total synthesis of the Strychnos alkaloid (+)-minfiensine has been accomplished. Prominent features of this synthesis include (i) a new enantioselective organocatalytic Diels-Alder/amine cyclization sequence to build the central tetracyclic pyrroloindoline framework in four steps from commercial materials and (ii) a 6-exo-dig radical cyclization to forge the final piperidinyl ring system. This total synthesis of (+)-minfiensine was completed in nine chemical steps and 21% overall yield.
Jones
Spencer B
SB
Merck Center for Catalysis at Princeton University, Princeton, New Jersey 08544, USA.
Simmons
Bryon
B
MacMillan
David W C
DW
D000470:Alkaloids / Q000737:chemistry; D000588:Amines / Q000737:chemistry; D002227:Carbazoles / Q000138:chemical synthesis*; D003500:Cyclization; D007536:Isomerism; D015394:Molecular Structure; D014748:Vinca Alkaloids / Q000737:chemistry
D000470:Alkaloids; D000588:Amines; D002227:Carbazoles; D014748:Vinca Alkaloids; C504098:minfiensine; C543267:vincorine; C001133:echitamine