Total Synthesis of the Myrioneuron Alkaloid (−)‐Schoberine B and Its Enantiomer (+)‐Schoberine B

Abstract

AbstractA dynamic kinetic asymmetric transformation, involving the generation of four stereogenic centers with a well‐defined configuration, occurs in the cyclocondensation of diastereomeric mixtures of 2‐oxocyclohexanepropionic acid racemates 6 with (1S,2R)‐cis‐aminoindanol: two major tetracyclic lactams, 7 a and 7 b, that differ in the configuration of the four stereocenters on the decahydroquinoline moiety were obtained. From the above lactams, the removal of the chiral auxiliary, the introduction of a 2‐piperidone ring, and the closure of the diazine ring complete the first enantioselective total synthesis of the Myrioneuron alkaloid (−)‐schoberine B and its enantiomer (+)‐schoberine B.