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.
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Li et al. (Wed,) studied this question.
synapsesocial.com/papers/69d896046c1944d70ce072e8 — DOI: https://doi.org/10.1021/acs.orglett.6c01066
Jiaji Li
Shenyang Pharmaceutical University
Zhibin Zhao
Shenyang Pharmaceutical University
Peiyuan Yang
Shenyang Pharmaceutical University
Organic Letters
Shenyang Pharmaceutical University
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