Efforts and Strategies for the Syntheses of Clavine‐Type Ergot Alkaloid Aurantioclavine

Aurantioclavine, isolated by Kozlovskii from Penicillium aurantiovirens, is a unique member of the 3,4‐disubstituted indole alkaloids distinguished by an azepino[5,4,3‐cd]indole. As an essential intermediate in the biosynthesis of the complex polycyclic alkaloids of the fungal communesin, it has att...

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Bibliographic Details
Published in:European journal of organic chemistry 2022-11, Vol.2022 (44), p.n/a
Main Authors: Ji, Cong‐Bin, Hu, Xin, Jiang, Shi‐Zhi, Yang, Jin‐Hui
Format: Article
Language:English
Subjects:
Alkaloids
Aurantioclavine
Biosynthesis
Formal synthesis
Fungi
Indole
Total synthesis
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Summary:Aurantioclavine, isolated by Kozlovskii from Penicillium aurantiovirens, is a unique member of the 3,4‐disubstituted indole alkaloids distinguished by an azepino[5,4,3‐cd]indole. As an essential intermediate in the biosynthesis of the complex polycyclic alkaloids of the fungal communesin, it has attracted considerable attention as a synthetic target. The development of various synthetic strategies for their application in total synthesis has been described. An overview focused on the synthesis of aurantioclavine from its first synthesis to the most recent one is present. This focus review presented recent advances in the synthesis of aurantioclavine, with a particular emphasis on synthetic strategies for building the azepino[5,4,3‐cd]indole framework via three key intermediates: 4‐substituted tryptamine/tryptophan derivatives, 4‐substituted tryptophol derivatives, and aniline & analogues.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.202201000