合成诺托酰胺 J：几种芳基取代吲哚生物碱生物合成中的一个潜在关键中间体。
Synthesis of notoamide J: a potentially pivotal intermediate in the biosynthesis of several prenylated indole alkaloids.
机构信息
Department of Chemistry, Colorado State University, Fort Collins, Colorado 80523, USA.
出版信息
J Org Chem. 2010 May 7;75(9):2785-9. doi: 10.1021/jo100332c.
Abstract
An efficient total synthesis of notoamide J, a new prenylated indole alkaloid and potential biosynthetic precursor, is described herein. Starting from L-proline and a substituted tryptophan derivative, this synthesis also employs an oxidation and pinacol rearrangement for the formation of the oxindole in the final step.
摘要
本文描述了一种新型的烯丙基吲哚生物碱和潜在生物合成前体——notoamide J 的高效全合成。该合成以 L-脯氨酸和取代色氨酸衍生物为起始原料，最后一步通过氧化和频哪醇重排形成了吲哚酮。
相似文献
1
Synthesis of notoamide J: a potentially pivotal intermediate in the biosynthesis of several prenylated indole alkaloids.合成诺托酰胺 J：几种芳基取代吲哚生物碱生物合成中的一个潜在关键中间体。
J Org Chem. 2010 May 7;75(9):2785-9. doi: 10.1021/jo100332c.
2
Studies on the biosynthesis of the notoamides: synthesis of an isotopomer of 6-hydroxydeoxybrevianamide E and biosynthetic incorporation into notoamide J.关于诺托酰胺生物合成的研究：6-羟基去氧布雷文酰胺 E 的同位素类似物的合成及生物合成掺入到诺托酰胺 J 中。
J Org Chem. 2011 Aug 5;76(15):5954-8. doi: 10.1021/jo200218a. Epub 2011 Jun 28.
3
Unified Approach to the Spiro(pyrrolidinyl-oxindole) and Hexahydropyrrolo[2,3-b]indole Alkaloids: Total Syntheses of Pseudophrynamines 270 and 272A.统一的 Spiro(pyrrolidinyl-oxindole) 和六氢吡咯并[2,3-b]吲哚生物碱方法：伪石蒜胺 270 和 272A 的全合成。
Org Lett. 2015 Dec 4;17(23):5922-5. doi: 10.1021/acs.orglett.5b03082. Epub 2015 Nov 24.
4
Biochemical characterization of NotB as an FAD-dependent oxidase in the biosynthesis of notoamide indole alkaloids.NotB 在诺托酰胺吲哚生物碱生物合成中作为 FAD 依赖性氧化酶的生化特征。
J Am Chem Soc. 2012 Jan 18;134(2):788-91. doi: 10.1021/ja2093212. Epub 2011 Dec 28.
5
Biomimetic and Concise Total Syntheses of Prenylated and Bicyclo[2.2.2]diazaoctane-Containing Indole Alkaloids Including Taichunamide A, Notoamide N and Versicolamide B.仿生简洁全合成含取代和双环[2.2.2]二氮杂辛烷的吲哚生物碱包括台长春酰胺 A、野百合碱 N 和长春花酰胺 B。
J Org Chem. 2024 Sep 6;89(17):12639-12650. doi: 10.1021/acs.joc.4c01559. Epub 2024 Aug 23.
6
Flavin-Dependent Monooxygenases NotI and NotI' Mediate Spiro-Oxindole Formation in Biosynthesis of the Notoamides.黄素依赖单加氧酶 NotI 和 NotI' 介导了诺托酰胺生物合成中的螺环-氧吲哚的形成。
Chembiochem. 2020 Sep 1;21(17):2449-2454. doi: 10.1002/cbic.202000004. Epub 2020 May 14.
7
Isolation of notoamide E, a key precursor in the biosynthesis of prenylated indole alkaloids in a marine-derived fungus, Aspergillus sp.从海洋来源的真菌曲霉属（Aspergillus sp.）中分离出诺托酰胺E，它是异戊烯基化吲哚生物碱生物合成中的关键前体。
J Am Chem Soc. 2009 Mar 25;131(11):3834-5. doi: 10.1021/ja810029b.
8
Rapid access to spirocyclic oxindole alkaloids: application of the asymmetric palladium-catalyzed [3 + 2] trimethylenemethane cycloaddition.快速获取螺环氧化吲哚生物碱：不对称钯催化的[3 + 2]三亚甲基甲烷环加成反应的应用
J Am Chem Soc. 2013 Nov 6;135(44):16720-35. doi: 10.1021/ja409013m.
9
Synthesis and bioconversions of notoamide T: a biosynthetic precursor to stephacidin A and notoamide B.合成和生物转化 notoaMide T：斯蒂芬酸 A 和 notoaMide B 的生物合成前体。
Org Lett. 2013 Jan 4;15(1):22-5. doi: 10.1021/ol302901p. Epub 2012 Dec 18.
10
Genome-based characterization of two prenylation steps in the assembly of the stephacidin and notoamide anticancer agents in a marine-derived Aspergillus sp.基于基因组的特征分析表明，在海洋来源的曲霉属真菌中， Stephacidin 和 Notoamide 抗癌剂的装配过程中存在两步异戊烯基化步骤。
J Am Chem Soc. 2010 Sep 15;132(36):12733-40. doi: 10.1021/ja1049302.
引用本文的文献
1
The Mutually Inspiring Biological and Chemical Synthesis of Fungal Bicyclo[2.2.2]diazaoctane Indole Alkaloids.真菌双环[2.2.2]二氮杂辛烷吲哚生物碱的生物与化学合成相互启发
Chem Rev. 2025 Feb 26;125(4):1718-1804. doi: 10.1021/acs.chemrev.4c00250. Epub 2025 Feb 10.
2
Structural and stereochemical diversity in prenylated indole alkaloids containing the bicyclo[2.2.2]diazaoctane ring system from marine and terrestrial fungi.海洋和陆地真菌中含双环[2.2.2]辛烷环系统的prenylated indole alkaloids 的结构和立体化学多样性。
Nat Prod Rep. 2018 Jun 20;35(6):532-558. doi: 10.1039/c7np00042a.
3
Marine Indole Alkaloids.海洋吲哚生物碱
Mar Drugs. 2015 Aug 6;13(8):4814-914. doi: 10.3390/md13084814.
4
Palladium-catalyzed synthesis of N-tert-prenylindoles.钯催化的 N-叔戊基吲哚合成。
Org Lett. 2013 Jun 7;15(11):2798-801. doi: 10.1021/ol4011344. Epub 2013 May 28.
5
Synthesis and bioconversions of notoamide T: a biosynthetic precursor to stephacidin A and notoamide B.合成和生物转化 notoaMide T：斯蒂芬酸 A 和 notoaMide B 的生物合成前体。
Org Lett. 2013 Jan 4;15(1):22-5. doi: 10.1021/ol302901p. Epub 2012 Dec 18.
6
Biochemical characterization of NotB as an FAD-dependent oxidase in the biosynthesis of notoamide indole alkaloids.NotB 在诺托酰胺吲哚生物碱生物合成中作为 FAD 依赖性氧化酶的生化特征。
J Am Chem Soc. 2012 Jan 18;134(2):788-91. doi: 10.1021/ja2093212. Epub 2011 Dec 28.
7
Lessons and revelations from biomimetic syntheses.仿生合成的经验与启示。
Nat Chem Biol. 2011 Nov 15;7(12):865-75. doi: 10.1038/nchembio.709.
8
Studies on the Biosynthesis of the Stephacidin and Notoamide Natural Products: A Stereochemical and Genetic Conundrum.斯蒂芬酸菌素和诺托酰胺天然产物的生物合成研究：一个立体化学和遗传学难题。
Isr J Chem. 2011 Apr;51(3):442-452. doi: 10.1002/ijch.201100016.
9
Studies on the biosynthesis of the notoamides: synthesis of an isotopomer of 6-hydroxydeoxybrevianamide E and biosynthetic incorporation into notoamide J.关于诺托酰胺生物合成的研究：6-羟基去氧布雷文酰胺 E 的同位素类似物的合成及生物合成掺入到诺托酰胺 J 中。
J Org Chem. 2011 Aug 5;76(15):5954-8. doi: 10.1021/jo200218a. Epub 2011 Jun 28.
本文引用的文献
1
Asymmetric total syntheses of (+)- and (-)-versicolamide B and biosynthetic implications.（+）-和（-）-变色胺 B 的不对称全合成及生物合成意义。
Nat Chem. 2009 Apr;1(1):63-8. doi: 10.1038/nchem.110.
2
Isolation of notoamide E, a key precursor in the biosynthesis of prenylated indole alkaloids in a marine-derived fungus, Aspergillus sp.从海洋来源的真菌曲霉属（Aspergillus sp.）中分离出诺托酰胺E，它是异戊烯基化吲哚生物碱生物合成中的关键前体。
J Am Chem Soc. 2009 Mar 25;131(11):3834-5. doi: 10.1021/ja810029b.
3
Isolation of antipodal (-)-versicolamide B and notoamides L-N from a marine-derived Aspergillus sp.从一株海洋来源的曲霉中分离出对映体（-）-杂色酰胺B和诺托酰胺L-N
Org Lett. 2009 Mar 19;11(6):1297-300. doi: 10.1021/ol900071c.
4
Notoamides F-K, prenylated indole alkaloids isolated from a marine-derived Aspergillus sp.诺托酰胺F-K，从海洋来源的曲霉属真菌中分离得到的异戊烯基化吲哚生物碱
J Nat Prod. 2008 Dec;71(12):2064-7. doi: 10.1021/np800471y.
5
Isolation, structure elucidation, and biomimetic total synthesis of versicolamide B, and the isolation of antipodal (-)-stephacidin A and (+)-notoamide B from Aspergillus versicolor NRRL 35600.杂色曲菌素B的分离、结构解析及仿生全合成，以及从杂色曲霉NRRL 35600中分离出对映体（-）-斯蒂芬菌素A和（+）-诺托酰胺B。
Angew Chem Int Ed Engl. 2008;47(19):3573-7. doi: 10.1002/anie.200800106.
6
Biomimetic total synthesis of malbrancheamide and malbrancheamide B.麦氏酰胺和麦氏酰胺B的仿生全合成
J Org Chem. 2008 Apr 18;73(8):3116-9. doi: 10.1021/jo800116y. Epub 2008 Mar 18.
7
Notoamides A-D: prenylated indole alkaloids isolated from a marine-derived fungus, Aspergillus sp.诺托酰胺A-D：从海洋来源真菌曲霉属（Aspergillus sp.）中分离得到的异戊烯基化吲哚生物碱
Angew Chem Int Ed Engl. 2007;46(13):2254-6. doi: 10.1002/anie.200604381.
8
A concise total synthesis of the notoamides C and D.noto酰胺C和D的简洁全合成。
Angew Chem Int Ed Engl. 2007;46(13):2257-61. doi: 10.1002/anie.200604377.
9
Paraherquamides, brevianamides, and asperparalines: laboratory synthesis and biosynthesis. An interim report.副赫夸米德、短链酰胺和曲霉帕拉菌素：实验室合成与生物合成。中期报告。
Acc Chem Res. 2003 Feb;36(2):127-39. doi: 10.1021/ar020229e.
10
Total synthesis of (-)-fumiquinazolines A, B, C, E, H, and I. Approaches to the synthesis of fiscalin A.(-)-烟曲霉喹唑啉A、B、C、E、H和I的全合成。法斯克林A的合成方法。
J Org Chem. 2003 Jan 24;68(2):545-63. doi: 10.1021/jo0264980.
Zotero 插件