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卤氯灵和海石竹酸的不对称全合成策略。

Asymmetric total synthesis strategies of halichlorine and pinnaic acid.

作者信息

Liu Lu, Jiang Minghua, Zhang Qingkang, Chen Hong, Zhang Yifu, Zhang Jian

机构信息

School of Pharmacy, Gansu University of Chinese Medicine Lanzhou 730000 P. R. China

Northwest Collaborative Innovation Center for Traditional Chinese Medicine Co-Constructed by Gansu Province & MOE of PRC Lanzhou 730000 P. R. China.

出版信息

RSC Adv. 2023 Nov 17;13(48):33754-33769. doi: 10.1039/d3ra06955a. eCollection 2023 Nov 16.

DOI:10.1039/d3ra06955a
PMID:38019985
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC10654894/
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.

摘要

卤氯灵和松节藻酸是从不同海洋生物中分离出来的结构相关的天然生物碱。这两种具有6-氮杂螺[4.5]癸烷骨架的海洋生物碱表现出广泛的生物学效应。正是这种独特的结构和潜在的有价值的生物活性引发了强烈的合成兴趣，使其成为近年来的研究热点。自从达尼谢夫斯基小组首次完成卤氯灵和松节藻酸的全合成以来，许多小组都报道了它们出色的合成方法，尤其是不对称合成策略。本文综述了以6-氮杂螺[4.5]癸烷骨架为关键中间体的卤氯灵和松节藻酸的不对称合成策略，可为相关工作提供一些指导。

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