STABLE CONFORMATION OF 2, 6-CIS-DISUBSTITUTED 1-ACYL-1, 2, 3, 6-TETRAHYDROPYRIDINES AND STEREOSELECTIVE FORMATION OF PALUSTRINE SIDE CHAIN

Abstract

The 1-acyl-2, 6-cis-disubstituted 1, 2, 3, 6-tetrahydropyridine derivatives (5a-5d) were found to possess the structure of 5-A as a stable conformer. This knowledge was applied to a stereo-controlled formation of the side chain of palustrine (1) by causing an aldehyde (8) to react with Et₂CuLi. A chelated intermediate (8-C) may play an important role in the preferential production of the desired compound (9).