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β-羟基硫化物及其合成方法。

β-Hydroxy sulfides and their syntheses.

作者信息

Marakalala Mokgethwa Bruce, Mmutlane Edwin M, Kinfe Henok H

机构信息

Department of Chemistry, University of Johannesburg, PO Box 524, Auckland Park 2006, South Africa.

出版信息

Beilstein J Org Chem. 2018 Jul 5;14:1668-1692. doi: 10.3762/bjoc.14.143. eCollection 2018.

DOI:10.3762/bjoc.14.143
PMID:30013693
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC6036969/
Abstract

Sulfur-containing natural products are ubiquitous in nature, their most abundant source being marine organisms since sulfur, in the form of the sulfate ion, is the second most abundant anion in sea water after chloride. As part of natural products, sulfur can appear in a multitude of combinations and oxidation states: thiol, sulfide (acyclic or heterocyclic), disulfide, sulfoxide, sulfonate, thioaminal, hemithioacetal, various thioesters, thiocarbamate and isothiocyanate. This review article focuses on β-hydroxy sulfides and analogs; their presence in natural products, general protocols for their synthesis, and examples of their application in target oriented synthesis.

摘要

含硫天然产物在自然界中普遍存在，其最丰富的来源是海洋生物，因为硫酸根离子形式的硫是海水中仅次于氯离子的第二丰富阴离子。作为天然产物的一部分，硫可以以多种组合和氧化态出现：硫醇、硫化物（无环或杂环）、二硫化物、亚砜、磺酸盐、硫代缩醛胺、半硫代乙缩醛、各种硫酯、硫代氨基甲酸盐和异硫氰酸酯。这篇综述文章重点关注β-羟基硫化物及其类似物；它们在天然产物中的存在、合成的一般方法以及它们在目标导向合成中的应用实例。

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4
Three Diketopiperazine Alkaloids with Spirocyclic Skeletons and One Bisthiodiketopiperazine Derivative from the Mangrove-Derived Endophytic Fungus Penicillium brocae MA-231.从红树林来源的内生真菌布罗卡青霉MA-231中分离得到的三种具有螺环骨架的二酮哌嗪生物碱和一种双硫代二酮哌嗪衍生物。
Org Lett. 2016 Oct 21;18(20):5304-5307. doi: 10.1021/acs.orglett.6b02620. Epub 2016 Oct 10.
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Synthesis of β-Hydroxysulfides from Thiophenols and Disulfides with tert-Butyl Hydroperoxide as the Oxidant and Reactant.以叔丁基过氧化氢为氧化剂和反应物，由苯硫酚和二硫化物合成β-羟基硫醚
ChemistryOpen. 2016 May 17;5(4):315-8. doi: 10.1002/open.201600023. eCollection 2016 Aug.
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Organocatalytic enantioselective desymmetrisation.有机催化的对映选择性去对称化。
Chem Soc Rev. 2016 Oct 21;45(20):5474-5540. doi: 10.1039/c5cs00015g. Epub 2016 Jun 27.
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Condensation of Macrocyclic Polyketides Produced by Penicillium sp. DRF2 with Mercaptopyruvate Represents a New Fungal Detoxification Pathway.DRF2 青霉所产生的大环聚酮化合物与巯基丙酮酸缩合，代表了一种新的真菌解毒途径。
J Nat Prod. 2016 Jun 24;79(6):1668-78. doi: 10.1021/acs.jnatprod.6b00295. Epub 2016 May 26.
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Ulbactins F and G, Polycyclic Thiazoline Derivatives with Tumor Cell Migration Inhibitory Activity from Brevibacillus sp.乌尔巴汀F和G，来自短短芽孢杆菌属的具有肿瘤细胞迁移抑制活性的多环噻唑啉衍生物
Org Lett. 2016 Apr 1;18(7):1658-61. doi: 10.1021/acs.orglett.6b00531. Epub 2016 Mar 21.
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Grisemycin, a Bridged Angucyclinone with a Methylsulfinyl Moiety from a Marine-Derived Streptomyces sp.灰色链霉菌来源的含亚砜基桥环 Angucyclinone 类抗生素格里霉素
Org Lett. 2016 Mar 18;18(6):1402-5. doi: 10.1021/acs.orglett.6b00332. Epub 2016 Mar 9.
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Leukotriene E4 is a full functional agonist for human cysteinyl leukotriene type 1 receptor-dependent gene expression.白三烯E4是一种对人半胱氨酰白三烯1型受体依赖性基因表达具有完全功能的激动剂。
Sci Rep. 2016 Feb 2;6:20461. doi: 10.1038/srep20461.