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Diversity oriented multi-component reaction (DOS–MCR) approach to access natural product analogues: regio- and chemo-selective synthesis of polyheterocyclic scaffolds via one-pot cascade reactions

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Abstract

Skeletally diverse and complex aza-cyclopenta(cd)diindene, pyrrolo(3,4-d)pyridine-13-carboxamide, and furo-pyrrolo(1,2-a)imidazole-4-carboxamide fused polyheterocyclic hybrid scaffolds and a furo(2,3-b)furan core have been accessed via one-pot three-component reaction by exploiting the build/couple/pair strategy of diversity oriented synthesis (DOS). This protocol is metal free, has a good substrate scope and affords products with good to excellent yields and regio- and chemo-selectivity. The heterocyclic skeletons obtained in this study mimic natural products such as eupolauramine, gracilamine and presilphiperfolanol.

Graphical abstract: Diversity oriented multi-component reaction (DOS–MCR) approach to access natural product analogues: regio- and chemo-selective synthesis of polyheterocyclic scaffolds via one-pot cascade reactions

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Supplementary files

Article information


Submitted
19 Feb 2020
Accepted
16 Mar 2020
First published
17 Mar 2020

Org. Biomol. Chem., 2020, Advance Article
Article type
Paper

Diversity oriented multi-component reaction (DOS–MCR) approach to access natural product analogues: regio- and chemo-selective synthesis of polyheterocyclic scaffolds via one-pot cascade reactions

L. Palanivel and V. Gnanasambandam, Org. Biomol. Chem., 2020, Advance Article , DOI: 10.1039/D0OB00368A

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