Issue 9, 2022

Total synthesis of monoterpenoid indole alkaloid (–)-arbophyllidine

Abstract

The first asymmetric total synthesis of indole alkaloid arbophyllidine has been accomplished. The synthesis features an intramolecular reductive Heck reaction to install the key quaternary carbon center and a Fischer indolization to efficiently construct the tetracyclic skeleton. Moreover, a novel NaClO2-mediated oxidative lactonization was achieved via selective oxidation at C-16 of the tetracyclic aldehyde. Density functional theory calculations provided an incisive understanding of the oxidative lactonization.

Graphical abstract: Total synthesis of monoterpenoid indole alkaloid (–)-arbophyllidine

Supplementary files

Article information

Article type
Research Article
Submitted
20 feb 2022
Accepted
21 mar 2022
First published
30 mar 2022

Org. Chem. Front., 2022,9, 2328-2332

Total synthesis of monoterpenoid indole alkaloid (–)-arbophyllidine

H. Zhai, Z. Wang, K. Chen, T. Sun, J. Wei and Y. Wu, Org. Chem. Front., 2022, 9, 2328 DOI: 10.1039/D2QO00284A

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