通过 N-O 键形成合成 10-氮杂-9-氧杂卡利毒素
Synthesis of 10-Aza-9-oxakalkitoxin by N-O Bond Formation.
机构信息
Department of Pharmaceutical and Biomedical Sciences, University of Georgia, 250 West Green Street, Athens, Georgia 30602, United States.
Department of Chemistry, University of Georgia, 140 Cedar Street, Athens, Georgia 30602, United States.
出版信息
Org Lett. 2022 Mar 11;24(9):1833-1836. doi: 10.1021/acs.orglett.2c00349. Epub 2022 Feb 28.
Abstract
We describe a formal synthesis of 10-aza-9-oxakalkitoxin, the hydroxalog of the cytotoxic marine natural product kalkitoxin, that features Mukaiyama Markovnikov silyl peroxidation of a terminal alkene and N-O bond formation as the central enabling steps.
摘要
我们描述了 10-氮杂-9-氧杂卡利毒素的一种全合成方法，卡利毒素是一种具有细胞毒性的海洋天然产物，它的羟化产物，其特征步骤是 Mukaiyama Markovnikov 硅基过氧化末端烯烃和 N-O 键形成。
相似文献
1
Synthesis of 10-Aza-9-oxakalkitoxin by N-O Bond Formation.通过 N-O 键形成合成 10-氮杂-9-氧杂卡利毒素
Org Lett. 2022 Mar 11;24(9):1833-1836. doi: 10.1021/acs.orglett.2c00349. Epub 2022 Feb 28.
2
Synthesis, Cytotoxicity, and Genotoxicity of 10-Aza-9-oxakalkitoxin, an ,,-Trisubstituted Hydroxylamine Analog, or Hydroxalog, of a Marine Natural Product.10-氮杂-9-氧杂卡莱毒素的合成、细胞毒性和遗传毒性研究，一种海洋天然产物的β-三取代羟胺类似物或羟氨类似物。
J Am Chem Soc. 2020 May 20;142(20):9147-9151. doi: 10.1021/jacs.0c03763. Epub 2020 May 7.
3
Formal Hydrotrimethylsilylation of Styrenes with Anti-Markovnikov Selectivity Using Hexamethyldisilane.使用六甲基二硅烷对苯乙烯进行反马氏选择性的正式氢三甲基硅烷化。
Org Lett. 2022 Dec 9;24(48):8735-8740. doi: 10.1021/acs.orglett.2c03170. Epub 2022 Nov 24.
4
The Mukaiyama aldol reaction of in situ generated nitrosocarbonyl compounds: selective C-N bond formation and N-O bond cleavage in one-pot for α-amination of ketones.原位生成的亚硝基羰基化合物的向山羟醛反应：一锅法中酮的α-胺化反应里选择性的C-N键形成和N-O键断裂
Chem Commun (Camb). 2015 Sep 21;51(73):13976-9. doi: 10.1039/c5cc05459a. Epub 2015 Aug 6.
5
Catalytic Properties of [PSiP] Pincer Cobalt(II) Chlorides Supported by Trimethylphosphine for Alkene Hydrosilylation Reactions.三甲基膦支持的[PSiP]钳形氯化钴（II）对烯烃硅氢化反应的催化性能
Inorg Chem. 2024 May 13;63(19):8807-8815. doi: 10.1021/acs.inorgchem.4c00521. Epub 2024 Apr 30.
6
Development and Application of Asymmetric Organocatalytic Mukaiyama and Vinylogous Mukaiyama-Type Reactions.不对称有机催化 Mukaiyama 和 vinylogous Mukaiyama 型反应的发展与应用。
Chemistry. 2018 Aug 1;24(43):10906-10933. doi: 10.1002/chem.201801866. Epub 2018 Jul 6.
7
The formyloxyl radical: electrophilicity, C-H bond activation and anti-Markovnikov selectivity in the oxidation of aliphatic alkenes.甲酰氧基自由基：脂肪族烯烃氧化反应中的亲电性、C-H键活化及反马氏选择性
Chem Sci. 2020 Oct 2;11(42):11584-11591. doi: 10.1039/d0sc04936k.
8
Formal total synthesis of N-methylmaysenine.N-甲基美森宁的形式全合成。
Org Lett. 2009 Apr 16;11(8):1809-12. doi: 10.1021/ol900384u.
9
Organocatalytic Enantioselective Mukaiyama-Mannich Reaction of Isatin-Derived Ketimines for the Synthesis of Oxindolyl-β -Amino Acid Esters.有机催化对映选择性Mukaiyama-Mannich 反应的色酮衍生的亚胺用于合成吲哚啉-β-氨基酸酯。
Chemistry. 2019 Nov 18;25(64):14688-14693. doi: 10.1002/chem.201903512. Epub 2019 Oct 16.
10
Formal Aza-Wacker Cyclization by Tandem Electrochemical Oxidation and Copper Catalysis.通过串联电化学氧化和铜催化实现的形式上的氮杂瓦克环化反应
Angew Chem Int Ed Engl. 2019 Mar 26;58(14):4700-4704. doi: 10.1002/anie.201814509. Epub 2019 Feb 27.
引用本文的文献
1
Intramolecular N-O Bond Formation for the Synthesis of -Alkyl and -Aryl Isoxazolidines.用于合成α-烷基和α-芳基异恶唑烷的分子内N-O键形成
J Am Chem Soc. 2025 Jun 18;147(24):21053-21059. doi: 10.1021/jacs.5c06061. Epub 2025 Jun 5.
2
Ammonium Dinitramide as a Prospective N-NO Synthon: Electrochemical Synthesis of Nitro--Azoxy Compounds from Nitrosoarenes.二硝酰胺铵作为一种潜在的N-NO合成子：由亚硝基芳烃电化学合成硝基-偶氮氧基化合物
Molecules. 2024 Nov 25;29(23):5563. doi: 10.3390/molecules29235563.
3
Synthesis of -Alkyl-1,3-dihydro-2,1-benzisoxazoles.α-烷基-1,3-二氢-2,1-苯并异恶唑的合成
Org Lett. 2024 Nov 15;26(45):9722-9727. doi: 10.1021/acs.orglett.4c03509. Epub 2024 Nov 5.
4
Discovery of a Hydroxylamine-Based Brain-Penetrant EGFR Inhibitor for Metastatic Non-Small-Cell Lung Cancer.基于羟胺的穿透血脑屏障的表皮生长因子受体抑制剂治疗转移性非小细胞肺癌的发现。
J Med Chem. 2023 Nov 23;66(22):15477-15492. doi: 10.1021/acs.jmedchem.3c01669. Epub 2023 Nov 7.
5
Recent Advances in the Synthesis of Di- and Trisubstituted Hydroxylamines.二取代和三取代羟胺的合成新进展。
Molecules. 2023 Mar 21;28(6):2816. doi: 10.3390/molecules28062816.
6
The -Trisubstituted Hydroxylamine Isostere and Its Influence on Lipophilicity and Related Parameters.三取代羟胺电子等排体及其对亲脂性和相关参数的影响。
ACS Med Chem Lett. 2022 Apr 20;13(5):799-806. doi: 10.1021/acsmedchemlett.1c00713. eCollection 2022 May 12.
本文引用的文献
1
Synthesis of --Butyl--disubstituted Hydroxylamines by N-O Bond Formation.通过形成N-O键合成β-丁基-二取代羟胺
Org Lett. 2021 Aug 20;23(16):6396-6400. doi: 10.1021/acs.orglett.1c02215. Epub 2021 Jul 30.
2
Diversity-Oriented Synthesis of ,,Trisubstituted Hydroxylamines from Alcohols and Amines by N-O Bond Formation.通过 N-O 键形成，从醇和胺出发，对,,,三取代羟胺进行导向多元化合成。
J Am Chem Soc. 2020 Sep 2;142(35):14820-14825. doi: 10.1021/jacs.0c05991. Epub 2020 Aug 24.
3
Synthesis, Cytotoxicity, and Genotoxicity of 10-Aza-9-oxakalkitoxin, an ,,-Trisubstituted Hydroxylamine Analog, or Hydroxalog, of a Marine Natural Product.10-氮杂-9-氧杂卡莱毒素的合成、细胞毒性和遗传毒性研究，一种海洋天然产物的β-三取代羟胺类似物或羟氨类似物。
J Am Chem Soc. 2020 May 20;142(20):9147-9151. doi: 10.1021/jacs.0c03763. Epub 2020 May 7.
4
Programmable Synthesis of 2-Deoxyglycosides.可编程合成 2-脱氧糖苷。
J Am Chem Soc. 2019 May 22;141(20):8098-8103. doi: 10.1021/jacs.9b03982. Epub 2019 May 9.
5
Synthesis of Trialkylhydroxylamines by Stepwise Reduction of O-Acyl N,N-Disubstituted Hydroxylamines: Substituent Effects on the Reduction of O-(1-Acyloxyalkyl)hydroxylamines and on the Conformational Dynamics of N-Alkoxypiperidines.通过逐步还原 O-酰基 N,N-二取代羟胺合成三烷基羟胺：取代基对 O-(1-烷氧基烷基)羟胺还原和 N-烷氧基哌啶构象动力学的影响。
J Org Chem. 2017 May 19;82(10):5345-5353. doi: 10.1021/acs.joc.7b00717. Epub 2017 May 8.
6
Synthesis of N,N,O-Trisubstituted Hydroxylamines by Stepwise Reduction and Substitution of O-Acyl N,N-Disubstituted Hydroxylamines.通过逐步还原和取代 O-酰基 N,N-二取代羟胺合成 N,N,O-三取代羟胺。
Org Lett. 2016 Apr 15;18(8):1820-3. doi: 10.1021/acs.orglett.6b00556. Epub 2016 Apr 7.
7
Synthesis of Ethers via Reaction of Carbanions and Monoperoxyacetals.通过碳负离子与单过氧缩醛反应合成醚类。
J Org Chem. 2015 Dec 18;80(24):12100-14. doi: 10.1021/acs.joc.5b02043. Epub 2015 Dec 7.
8
Total Synthesis of (-)-Exiguolide.(-)-埃克西古内酯的全合成
Org Lett. 2015 Oct 2;17(19):4706-9. doi: 10.1021/acs.orglett.5b02162.
9
Catalytic Enantioselective Peroxidation of α,β-Unsaturated Aldehydes for the Asymmetric Synthesis of Biologically Important Chiral Endoperoxides.用于生物重要手性内过氧化物不对称合成的α,β-不饱和醛的催化对映选择性过氧化反应
J Am Chem Soc. 2015 Jul 8;137(26):8400-3. doi: 10.1021/jacs.5b05345. Epub 2015 Jun 29.
Zotero 插件