A general asymmetric route to trans- or cis.2,6-disubstituted piperidine. First total synthesis of (+)-9-epi-6-epipinidinol and (-)- pinidinol

Article abstract of DOI:10.1016/S0040-4020(98)00831-X

Starting from 1,6-heptadiene, two AD reactions in a stepwise manner lead to the anti-1,5-diol and syn-1,5-diol stereodivergently, which have been converted by aminocyclization into trans- and cis-2,6-disubstituted piperidines (trans- and cis-12), respectively. The first total synthesis of (+)-9-epi-6-epipinidinol (2) and (-)-pinidinol (3) has been achieved from trans- and cis-12.