Total synthesis of (−)-securingine G

Abstract

In this study, we present the first total synthesis of (−)-securingine G. Diverging from the proposed biosynthetic pathway, our approach involves the addition of nucleophilic pyridine anion species to the electrophilic menisdaurilide congener. Crucially, incorporating a weakly basic yet nucleophilic tri(2-pyridinyl)lanthanum complex proved essential to circumvent undesired base-mediated pathways during the key coupling reaction. Notably, we introduce n-Bu3La·5LiCl as a new exchange reagent, facilitating efficient halide/lanthanum exchange of (hetero)aryl halides.

Graphical abstract: Total synthesis of (−)-securingine G

Supplementary files

Article information

Article type
Communication
Submitted
07 Mar 2024
Accepted
22 May 2024
First published
23 May 2024

Chem. Commun., 2024, Advance Article

Total synthesis of (−)-securingine G

T. Youn, T. Kim and S. Han, Chem. Commun., 2024, Advance Article , DOI: 10.1039/D4CC01075B

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