A de novo Stereocontrolled Synthetic Approach to a Functionalized Indolizidine Core

Kiss, Loránd and Nonn, Melinda and Escorihuela, Jorge (2023) A de novo Stereocontrolled Synthetic Approach to a Functionalized Indolizidine Core. Synlett, 34 (02). pp. 163-167. ISSN 0936-5214

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Abstract

A convenient domino synthetic approach for the construction of the indolizidine core in diastereoselective manner has been developed from inexpensive starting compounds, providing triple functionalization. The novel synthetic route started from -lactam derived from 1,5-cyclooctadiene including a ring-opening metathesis/crossmetathesis sequence as key steps with methyl acrylate followed by intramolecular ring closure across an aza-Michael addition. The process gave functionalized indolizidine framework with stereocontrol in high yields. DFT calculations supported the experimentally observed stereoselective reaction.

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