海洋奥辛 A 和 B 的螺环亚胺部分的合成。
Synthesis of the spiroiminal moiety of marineosins A and B.
机构信息
Department of Chemistry MS 015, Brandeis University, Waltham, Massachusetts 02454-9110, USA.
出版信息
Org Lett. 2010 Apr 2;12(7):1600-3. doi: 10.1021/ol100333d.
Abstract
A model for the spiroiminal moiety of marineosins A and B was prepared starting from methylvalerolactone. Addition of vinylmagnesium bromide, protection of the alcohol, and reaction of the vinyl ketone with a protected pyrrole-2-carbonitrile N-oxide gave an isoxazoline. Hydrogenolysis of the N-O bond with Raney nickel gave a keto imine that cyclized to a hemi-iminal. O-Methylation, acid-catalyzed cleavage of the TES group and spiroiminal formation, and deprotection completed a seven-step synthesis.
摘要
从甲基戊内酯出发，制备了海洋霉素 A 和 B 的螺环亚胺部分的模型。加成乙烯基溴化镁，保护醇，然后将乙烯酮与保护的吡咯-2-腈 N-氧化物反应，得到异恶唑啉。用雷尼镍氢化 N-O 键得到酮亚胺，该酮亚胺环化得到半亚胺。O-甲基化、TES 基团的酸催化裂解和螺环亚胺的形成，以及脱保护完成了七步合成。
相似文献
1
Synthesis of the spiroiminal moiety of marineosins A and B.海洋奥辛 A 和 B 的螺环亚胺部分的合成。
Org Lett. 2010 Apr 2;12(7):1600-3. doi: 10.1021/ol100333d.
2
Synthesis of the spiroiminal moiety and approaches to the synthesis of marineosins A and B.螺环亚胺部分的合成及海洋霉素 A 和 B 的合成方法。
J Org Chem. 2013 Dec 6;78(23):12161-75. doi: 10.1021/jo402178r. Epub 2013 Nov 21.
3
A concise approach to the spiroiminal fragment of marineosins.海洋奥辛斯螺环片段的简洁方法。
Org Biomol Chem. 2013 May 14;11(18):2936-8. doi: 10.1039/c3ob40208h.
4
Synthesis of novel synthetic intermediates from the reaction of benzimidazole and triazole carbenes with ketenimines and their application in the construction of spiro-pyrroles.新型合成中间体的合成，来自苯并咪唑和三唑卡宾与烯酮亚胺的反应，及其在螺吡咯烷构建中的应用。
Org Biomol Chem. 2009 Dec 7;7(23):5010-9. doi: 10.1039/b915215f. Epub 2009 Oct 14.
5
Enantioselective functionalization of indoles and pyrroles via an in situ-formed spiro intermediate.通过原位形成的螺环中间体对吲哚和吡咯进行对映选择性官能化。
J Am Chem Soc. 2013 Jun 5;135(22):8169-72. doi: 10.1021/ja403535a. Epub 2013 May 20.
6
Organocatalytic Asymmetric Michael/Friedel-Crafts Cascade Reaction of 3-Pyrrolyl-oxindoles and α,β-Unsaturated Aldehydes for the Construction of Chiral Spiro[5,6-dihydropyrido[1,2-a]pyrrole-3,3'-oxindoles].3-吡咯基氧化吲哚与α,β-不饱和醛的有机催化不对称迈克尔/傅克串联反应用于构建手性螺[5,6-二氢吡啶并[1,2-a]吡咯-3,3'-氧化吲哚]
J Org Chem. 2015 Jun 5;80(11):5951-7. doi: 10.1021/acs.joc.5b00597. Epub 2015 May 26.
7
Facile synthesis of spiro[indoline-3,3'-pyrrolo[1,2-a]quinolines] and spiro[indoline-3,1'-pyrrolo[2,1-a]isoquinolines] via 1,3-dipolar cycloaddition reactions of heteroaromatic ammonium salts with 3-phenacylideneoxindoles.通过杂环铵盐与 3-苯甲酰亚甲基氧吲哚的 1,3-偶极环加成反应，简便合成螺[吲哚啉-3,3'-吡咯[1,2-a]喹啉]和螺[吲哚啉-3,1'-吡咯[2,1-a]异喹啉]。
Org Biomol Chem. 2012 Dec 21;10(47):9452-63. doi: 10.1039/c2ob26849c. Epub 2012 Nov 1.
8
Expedient and Divergent Tandem One-Pot Synthesis of Benz[e]indole and Spiro[indene-1,3'-pyrrole] Derivatives from Alkyne-Tethered Chalcones/Cinnamates and TosMIC.炔基桥连查尔酮/肉桂酸盐与对甲苯磺酰基甲基异腈一锅法高效构建苯并[e]吲哚和螺[吲哚-1,3'-吡咯]衍生物
Org Lett. 2015 Jul 17;17(14):3576-9. doi: 10.1021/acs.orglett.5b01676. Epub 2015 Jul 8.
9
Evaluation of the biosynthetic proposal for the synthesis of marineosins A and B.海洋霉素 A 和 B 生物合成方案的评估。
Org Lett. 2010 Mar 5;12(5):1048-51. doi: 10.1021/ol100034p.
10
Synthesis of substituted 1,4,5,6-tetrahydrocyclopenta[b]pyrroles by platinum-catalyzed cascade cyclization/ring expansion of 2-alkynyl-1-azaspiro[2.3]hexanes.通过铂催化的 2-炔基-1-氮杂螺[2.3]己烷的级联环化/环扩张合成取代的 1,4,5,6-四氢环戊并[b]吡咯。
J Org Chem. 2011 Jul 15;76(14):5813-20. doi: 10.1021/jo201000f. Epub 2011 Jun 21.
引用本文的文献
1
Marine Pyrrole Alkaloids.海洋吡咯生物碱。
Mar Drugs. 2021 Sep 10;19(9):514. doi: 10.3390/md19090514.
2
MarH, a Bifunctional Enzyme Involved in the Condensation and Hydroxylation Steps of the Marineosin Biosynthetic Pathway.MarH，一种参与海洋素生物合成途径缩合和羟化步骤的双功能酶。
Org Lett. 2017 Mar 17;19(6):1298-1301. doi: 10.1021/acs.orglett.7b00093. Epub 2017 Mar 8.
3
Structure, Chemical Synthesis, and Biosynthesis of Prodiginine Natural Products.灵菌红素天然产物的结构、化学合成及生物合成
Chem Rev. 2016 Jul 27;116(14):7818-53. doi: 10.1021/acs.chemrev.6b00024. Epub 2016 Jun 17.
4
Stereospecific synthesis of 23-hydroxyundecylprodiginines and analogues and conversion to antimalarial premarineosins via a Rieske oxygenase catalyzed bicyclization.23-羟基十一烷基灵菌红素及其类似物的立体定向合成以及通过赖氏氧化酶催化的双环化反应转化为抗疟前海生菌素。
J Org Chem. 2014 Dec 5;79(23):11674-89. doi: 10.1021/jo5023553. Epub 2014 Nov 18.
5
Elucidation of final steps of the marineosins biosynthetic pathway through identification and characterization of the corresponding gene cluster.通过鉴定和表征相应的基因簇来阐明海洋菌素生物合成途径的最后步骤。
J Am Chem Soc. 2014 Mar 26;136(12):4565-74. doi: 10.1021/ja411544w. Epub 2014 Mar 12.
6
Towards the Total Synthesis of Marineosin A: Construction of the Macrocyclic Pyrrole and an Advanced, Functionalized Spiroaminal Model.迈向海生素A的全合成：大环吡咯的构建及一个高级功能化螺胺模型
European J Org Chem. 2013 Jul 1;2013(20). doi: 10.1002/ejoc.201300643.
7
Synthesis of the spiroiminal moiety and approaches to the synthesis of marineosins A and B.螺环亚胺部分的合成及海洋霉素 A 和 B 的合成方法。
J Org Chem. 2013 Dec 6;78(23):12161-75. doi: 10.1021/jo402178r. Epub 2013 Nov 21.
8
Spiroaminal Model Systems of the Marineosins with Final Step Pyrrole Incorporation.含最终步骤吡咯掺入的海洋菌素的螺胺模型系统。
Tetrahedron Lett. 2013 May 1;54(18):2231-2234. doi: 10.1016/j.tetlet.2013.02.059.
本文引用的文献
1
Evaluation of the biosynthetic proposal for the synthesis of marineosins A and B.海洋霉素 A 和 B 生物合成方案的评估。
Org Lett. 2010 Mar 5;12(5):1048-51. doi: 10.1021/ol100034p.
2
Marineosins A and B, cytotoxic spiroaminals from a marine-derived actinomycete.海洋菌素A和B，源自海洋放线菌的细胞毒性螺旋氨基化合物。
Org Lett. 2008 Dec 18;10(24):5505-8. doi: 10.1021/ol8020644.
3
Elucidation of the Streptomyces coelicolor pathway to 2-undecylpyrrole, a key intermediate in undecylprodiginine and streptorubin B biosynthesis.天蓝色链霉菌合成2-十一烷基吡咯的途径解析，2-十一烷基吡咯是十一烷基灵菌红素和链霉红菌素B生物合成中的关键中间体。
Chem Biol. 2008 Feb;15(2):137-48. doi: 10.1016/j.chembiol.2007.11.015.
4
Anticancer and immunosuppressive properties of bacterial prodiginines.细菌灵菌红素的抗癌和免疫抑制特性。
Future Microbiol. 2007 Dec;2(6):605-18. doi: 10.2217/17460913.2.6.605.
5
The biosynthesis and regulation of bacterial prodiginines.细菌灵杆菌素的生物合成与调控
Nat Rev Microbiol. 2006 Dec;4(12):887-99. doi: 10.1038/nrmicro1531.
6
Chemistry and biology of roseophilin and the prodigiosin alkaloids: a survey of the last 2500 years.灵菌红素和灵菌红素生物碱的化学与生物学：过去2500年的综述
Angew Chem Int Ed Engl. 2003 Aug 11;42(31):3582-603. doi: 10.1002/anie.200300582.
7
Analysis of the prodiginine biosynthesis gene cluster of Streptomyces coelicolor A3(2): new mechanisms for chain initiation and termination in modular multienzymes.天蓝色链霉菌A3(2)的灵菌红素生物合成基因簇分析：模块化多酶中链起始和终止的新机制
Chem Biol. 2001 Aug;8(8):817-29. doi: 10.1016/s1074-5521(01)00054-0.
Zotero 插件