Highly Stereoselective Ugi/Pictet-Spengler Sequence.

J Org Chem

Department of Drug Design, University of Groningen, A. Deusinglaan 1, 9713 AV Groningen, The Netherlands.

Published: June 2022

Discovering novel synthetic routes for rigid nitrogen-containing polyheterocycles using sustainable, atom-economical, and efficient (= short) synthetic pathways is of high interest in organic chemistry. Here, we describe an operationally simple and short synthesis of the privileged scaffold dihydropyrrolo[1,2-]pyrazine-dione from readily accessible starting materials. The alkaloid-type polycyclic scaffold with potential bioactivity was achieved by a multicomponent reaction (MCR)-based protocol via a Ugi four-component reaction and Pictet-Spengler sequence under different conditions, yielding a diverse library of products.

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http://www.ncbi.nlm.nih.gov/pmc/articles/PMC9490873PMC
http://dx.doi.org/10.1021/acs.joc.2c00244DOI Listing

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