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克琳碱和血根碱类生物碱的化学合成:具有生物活性和对映体相关的系统,可作为展示分子组装新方法的载体。

The Chemical Synthesis of the Crinine and Haemanthamine Alkaloids: Biologically Active and Enantiomerically-Related Systems that Serve as Vehicles for Showcasing New Methodologies for Molecular Assembly.

机构信息

Institute for Advanced and Applied Chemical Synthesis, Jinan University, Zhuhai 519070, China.

出版信息

Molecules. 2021 Feb 2;26(3):765. doi: 10.3390/molecules26030765.

DOI:10.3390/molecules26030765
PMID:33540725
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC7867252/
Abstract

The title alkaloids, often referred to collectively as crinines, are a prominent group of structurally distinct natural products with additional members being reported on a regular basis. As such, and because of their often notable biological properties, they have attracted attention as synthetic targets since the mid-1950s. Such efforts continue unabated and more recent studies on these alkaloids have focused on using them as vehicles for showcasing the utility of new synthetic methods. This review provides a comprehensive survey of the nearly seventy-year history of these synthetic endeavors.

摘要

标题生物碱,通常统称为藜宁生物碱,是一组结构独特的天然产物,其成员经常被定期报道。因此,由于它们通常具有显著的生物特性,自 20 世纪 50 年代中期以来,它们一直作为合成目标引起人们的关注。这些努力仍在继续,最近对这些生物碱的研究集中在利用它们作为展示新合成方法效用的载体。本综述全面概述了这些合成工作近 70 年的历史。

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Sci Rep. 2019 Jun 11;9(1):8471. doi: 10.1038/s41598-019-44746-7.
6
Efficient Enantioselective Syntheses of Chiral Natural Products Facilitated by Ligand Design.通过配体设计促进手性天然产物的高效对映选择性合成。
Chem Rec. 2020 Jan;20(1):23-40. doi: 10.1002/tcr.201900003. Epub 2019 Apr 26.
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Derivatives of the β-Crinane Amaryllidaceae Alkaloid Haemanthamine as Multi-Target Directed Ligands for Alzheimer's Disease.β-石蒜科生物碱海曼他敏的衍生物作为阿尔茨海默病的多靶点定向配体。
Molecules. 2019 Apr 3;24(7):1307. doi: 10.3390/molecules24071307.
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Application of Electrocyclic Ring-Opening and Desymmetrizing Nucleophilic Trappings of meso-6,6-Dibromobicyclo[3.1.0]hexanes to Total Syntheses of Crinine and Haemanthamine Alkaloids.meso-6,6-二溴双环[3.1.0]己烷的电环化开环和非对称亲核捕获在刺桐灵和血根碱类生物碱的全合成中的应用。
J Org Chem. 2019 Mar 15;84(6):3431-3466. doi: 10.1021/acs.joc.9b00018. Epub 2019 Mar 4.
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Amaryllidaceae and Sceletium alkaloids.石蒜科和尸茄属生物碱。
Nat Prod Rep. 2019 Oct 16;36(10):1462-1488. doi: 10.1039/c8np00055g.
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Catalytic Asymmetric Total Syntheses of Naturally Occurring Amarylidaceae Alkaloids, (-)-Crinine, (-)- epi-Crinine, (-)-Oxocrinine, (+)- epi-Elwesine, (+)-Vittatine, and (+)- epi-Vittatine.天然石蒜科生物碱(-)-刺桐碱、(-)-表刺桐碱、(-)-氧化石蒜碱、(+)-表吴茱萸碱、(+)-维替汀碱和(+)-表维替汀碱的催化不对称全合成。
Org Lett. 2018 Aug 3;20(15):4421-4424. doi: 10.1021/acs.orglett.8b01703. Epub 2018 Jul 20.