Issue 1, 2023

A modular and divergent approach for the total synthesis of Elaeocarpus alkaloids

Abstract

Herein we report a unified strategy for the divergent total synthesis of six Elaeocarpus alkaloids in 6–10 steps from commercially available materials. This modular approach relied on the rapid construction of the tetrahydrobenzopyran-4-one framework through an aldol/dehydration/oxa-Michael process to set all carbons and functional groups ready for the core construction. A key NbCl5-mediated intramolecular Mannich reaction was used to build the C ring and secure both stereoisomers existing in these natural products. Finally, a diversification was achieved through the intermediacy of thioamide, with the side chain of elaeocarfoline A/B installed by an Eschenmoser sulfide contraction/reduction sequence.

Graphical abstract: A modular and divergent approach for the total synthesis of Elaeocarpus alkaloids

Supplementary files

Article information

Article type
Research Article
Submitted
13 Sep 2022
Accepted
05 Nov 2022
First published
08 Nov 2022

Org. Chem. Front., 2023,10, 68-73

A modular and divergent approach for the total synthesis of Elaeocarpus alkaloids

G. Tian, Y. Zhang, C. Qin and J. Wang, Org. Chem. Front., 2023, 10, 68 DOI: 10.1039/D2QO01460B

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