Collect. Czech. Chem. Commun. 1991, 56, 1309-1316
https://doi.org/10.1135/cccc19911309

Synthesis in the group of nuphar alkaloids. VII. An easy access to (-)-nupharamine

Andrzej Leniewski and Jerzy Szychowski

Department of Chemistry, Warsaw University Pasteura 1, 02-093 Warsaw, Poland

This article is part of serial Synthesis in the group of nuphar alkaloids.

Abstract

A simple and effective approach to the total synthesis of (-)-nupharamine (I) is presented, which allows to control the stereochemistry at C-3 by epimerization of the ethoxycarbonyl function. The key steps are reductive amination of the respective substituted 1,5-diketone V and enantiomer resolution of piperidine VI using (1S)-(-)-camphanic acid.