A FACILE SYNTHESIS OF (+/-)-SESBANINE VIA γ-ADDITION OF KETENE SILYL ACETAL WITH QUATERNIZED METHYL NICOTINATE

Article abstract of DOI:10.1016/S0040-4039(00)98168-1

Total synthesis of (+/-)-sesbanine (1) was carried out using γ-addition of ketene silyl acetal of methyl 3-cyclopentenecarboxylate to quaternized methyl nicotinate.The resulting 1,4-dihydropyridine (7) was oxidized with DDQ to give 4-substituted nicotinate (2) and 2 was converted to alcohol (8) by stereoselective oxymercuration followed by treatment with ammonia to give 1.