Stereoselective synthesis of a natural product inspired tetrahydroindolo[2,3-a]-quinolizine compound library

摘要

A natural product-inspired synthesis of a compound collection embodying the tetrahydroindolo [2,3-a] quinolizine scaffold was established with a five step synthesis route. An imino-Diels-Alder reaction between Danishefsky's diene and the iminoesters derived from tryptamines was used as a key reaction. Reductive amination of the ketone function and amide synthesis with the carboxylic acid derived from the ethyl ester, were used to decorate the core scaffold. Thus a compound library of 530 tetrahydroindolo[2,3-a]quinolizines was generated and submitted to European lead factory consortium for various biological screenings. (C) 2015 The Authors. Published by Elsevier Ltd. This is an open access article under the CC BY-NC-ND license (http://creativecommons.org/licenses/by-nc-nd/4.0/).