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

摘要

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. (C) 1998 Elsevier Science Ltd. All rights reserved. [References: 23]