Total Synthesis of Indigotinoline A and Enabled Stereochemical Revision of Isatindigotindoline B

Organic Letters 2026

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Authors: Jiaji Li, Zhibin Zhao, Peiyuan Yang, Mingquan Wang, Sen Zhang, Tianyu Lv, Lianjie Zhang, Lu Yang, Shaojiang Song, Xiaoxiao Huang, Yongxiang Liu
DOI: 10.1021/acs.orglett.6c01066
Cited by: 1
References: 39

Abstract

The first total synthesis of scarce alkaloid indigotinoline A from Isatis indigotica was achieved in six steps from a known carboxylic acid (13% overall yield). The distinctive 6/5/6/5/6 N, O -heterocycle was efficiently assembled via a one-pot triple cascade, Povarov-type cyclization, intramolecular substitution, and visible-light-mediated oxidative rearrangement, followed by bioinspired N-oxidation/1,2-migration. This synthesis also prompted re-examination of proposed biosynthetic precursor isatindigotindoline B, leading to revision of its stereochemistry based on spectroscopic analysis.

Fields of Study & Subjects

Quinazolinone synthesis and applications Plant-based Medicinal Research Alkaloids: synthesis and pharmacology

Publication details

Journal / source
Organic Letters
Publisher
American Chemical Society (ACS)
Volume
28
Issue
15
Pages
4969–4974
Publication date
8 April 2026
Language
EN