Concepedia

Eight‐Step Total Synthesis of Phalarine by Bioinspired Oxidative Coupling of Indole and Phenol

Lei Li, Kuo Yuan, Qianlan Jia, Yanxing Jia

Angewandte Chemie · 2019 · 13 citations · 46 references

DOI

Concepts

Abstract

Abstract We report for the first time that the benzofuro[3,2‐ b ]indoline framework could be obtained by PIDA‐mediated direct oxidative coupling of 2,3‐disubstituted‐indoles with phenols. Application of this chemistry allows for an eight‐step total synthesis of phalarine from commercially available tryptamine.

References

46

Hypervalent iodine-mediated phenol dearomatization in natural product synthesis

Laurent Pouységu, Denis Deffieux, Stéphane Quideau · Tetrahedron · 2010 · 642 citations

, , +7

Isolation and structure determination of diazonamides A and B, unusual cytotoxic metabolites from the marine ascidian Diazona chinensis

Niels Lindquist, William Fenical, Gregory D. Van Duyne et al. · Journal of the American Chemical Society · 1991 · 338 citations

, , +7

Hypervalent iodine(III): selective and efficient single-electron-transfer (SET) oxidizing agent

Toshifumi Dohi, Motoki Ito, Nobutaka Yamaoka et al. · Tetrahedron · 2009 · 249 citations

, , +10

A Concise and Flexible Total Synthesis of (−)‐Diazonamide A

Anthony W. G. Burgett, Qingyi Li, Wei Qi et al. · Angewandte Chemie International Edition · 2003 · 236 citations · Full text

, , +8

External oxidant-free electrooxidative [3 + 2] annulation between phenol and indole derivatives

Kun Liu, Shan Tang, Peng‐Fei Huang et al. · Nature Communications · 2017 · 193 citations · Full text

, , +15