Issue 48, 2023

Asymmetric total synthesis strategies of halichlorine and pinnaic acid

Abstract

Halichlorine and pinnaic acid are structurally related natural alkaloids isolated from different marine organisms. These two marine alkaloids bearing a 6-azaspiro[4.5]decane skeleton demonstrate a wide range of biological effects. It is this kind of unique structure and potentially valuable biological activity that have prompted strong synthetic interest, making it a research focus in recent years. Since the first total synthesis of halichlorine and pinnaic acid completed by Danishefsky's group, many groups have reported their outstanding synthesis methods especially the asymmetric synthesis strategies. This review summarizes the asymmetric synthesis strategies of halichlorine and pinnaic acid using a 6-azaspiro[4.5]decane skeleton as the key intermediate, which can provide some guidance for related work.

Graphical abstract: Asymmetric total synthesis strategies of halichlorine and pinnaic acid

Article information

Article type
Review Article
Submitted
12 Oct 2023
Accepted
09 Nov 2023
First published
17 Nov 2023
This article is Open Access
Creative Commons BY license

RSC Adv., 2023,13, 33754-33769

Asymmetric total synthesis strategies of halichlorine and pinnaic acid

L. Liu, M. Jiang, Q. Zhang, H. Chen, Y. Zhang and J. Zhang, RSC Adv., 2023, 13, 33754 DOI: 10.1039/D3RA06955A

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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