Issue 16, 2021

Nonbiomimetic total synthesis of indole alkaloids using alkyne-based strategies

Abstract

Biomimetic natural product synthesis is generally straightforward and efficient because of its established feasibility in nature and utility in comprehensive synthesis, and the cost-effectiveness of naturally derived starting materials. On the other hand, nonbiomimetic strategies can be an important option in natural product synthesis since (1) nonbiomimetic synthesis offers more flexibility and can demonstrate the originality of chemists, and (2) the structures of derivatives accessible by nonbiomimetic synthesis can be considerably different from those that are synthesised in nature. This review summarises nonbiomimetic total syntheses of indole alkaloids using alkyne chemistry for constructing core structures, including ergot alkaloids, monoterpene indole alkaloids (mainly corynanthe, aspidosperma, strychnos, and akuammiline), and pyrroloindole and related alkaloids. To clarify the differences between alkyne-based strategies and biosynthesis, the alkynes in nature and the biosyntheses of indole alkaloids are also outlined.

Graphical abstract: Nonbiomimetic total synthesis of indole alkaloids using alkyne-based strategies

Article information

Article type
Review Article
Submitted
26 Dec. 2020
Accepted
23 Marts 2021
First published
24 Marts 2021

Org. Biomol. Chem., 2021,19, 3551-3568

Nonbiomimetic total synthesis of indole alkaloids using alkyne-based strategies

H. Ohno and S. Inuki, Org. Biomol. Chem., 2021, 19, 3551 DOI: 10.1039/D0OB02577A

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