• 文献检索
  • 文档翻译
  • 深度研究
  • 学术资讯
  • Suppr Zotero 插件Zotero 插件
  • 邀请有礼
  • 套餐&价格
  • 历史记录
应用&插件
Suppr Zotero 插件Zotero 插件浏览器插件Mac 客户端Windows 客户端微信小程序
定价
高级版会员购买积分包购买API积分包
服务
文献检索文档翻译深度研究API 文档MCP 服务
关于我们
关于 Suppr公司介绍联系我们用户协议隐私条款
关注我们

Suppr 超能文献

核心技术专利:CN118964589B侵权必究
粤ICP备2023148730 号-1Suppr @ 2026

文献检索

告别复杂PubMed语法,用中文像聊天一样搜索,搜遍4000万医学文献。AI智能推荐,让科研检索更轻松。

立即免费搜索

文件翻译

保留排版,准确专业,支持PDF/Word/PPT等文件格式,支持 12+语言互译。

免费翻译文档

深度研究

AI帮你快速写综述,25分钟生成高质量综述,智能提取关键信息,辅助科研写作。

立即免费体验

对呋咱倍半萜醇的重塑:氧定向氧化曼尼希反应的发现。

Remodeling of fumagillol: discovery of an oxygen-directed oxidative Mannich reaction.

机构信息

Center for Chemical Methodology and Library Development, Boston University , 590 Commonwealth Avenue, Boston, Massachusetts 02215, United States.

出版信息

Org Lett. 2014 Feb 7;16(3):792-5. doi: 10.1021/ol4035269. Epub 2014 Jan 10.

DOI:10.1021/ol4035269
PMID:24410175
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC3927640/
Abstract

An efficient, two-step construction of highly complex alkaloid-like compounds from the natural product fumagillol is described. This approach, which mimics a biosynthetic cyclase/oxidase sequence, allows for rapid and efficient structure elaboration of the basic fumagillol scaffold with a variety of readily available coupling partners. Mechanistic experiments leading to the discovery of an oxygen-directed oxidative Mannich reaction are also described.

摘要

本文描述了一种从天然产物呋咱并[1,2-α]色满醇出发高效、两步构建高度复杂类似生物碱化合物的方法。这种方法模拟了生物合成环化酶/氧化酶序列,可快速有效地对呋咱并[1,2-α]色满醇基本骨架进行结构修饰,且可使用各种易得的偶联试剂。文中还描述了导致发现定向氧的氧化 Mannich 反应的机理实验。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5f93/3993848/a7c29e9f6cae/ol-2013-035269_0009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5f93/3993848/97be69cdd4a0/ol-2013-035269_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5f93/3993848/7e8cda4e473c/ol-2013-035269_0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5f93/3993848/c4b60ac976d8/ol-2013-035269_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5f93/3993848/84c291bb87cb/ol-2013-035269_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5f93/3993848/d3152963a2e5/ol-2013-035269_0006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5f93/3993848/1f5b3168ed6d/ol-2013-035269_0007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5f93/3993848/c58713895085/ol-2013-035269_0008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5f93/3993848/a7c29e9f6cae/ol-2013-035269_0009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5f93/3993848/97be69cdd4a0/ol-2013-035269_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5f93/3993848/7e8cda4e473c/ol-2013-035269_0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5f93/3993848/c4b60ac976d8/ol-2013-035269_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5f93/3993848/84c291bb87cb/ol-2013-035269_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5f93/3993848/d3152963a2e5/ol-2013-035269_0006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5f93/3993848/1f5b3168ed6d/ol-2013-035269_0007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5f93/3993848/c58713895085/ol-2013-035269_0008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5f93/3993848/a7c29e9f6cae/ol-2013-035269_0009.jpg

相似文献

1
Remodeling of fumagillol: discovery of an oxygen-directed oxidative Mannich reaction.对呋咱倍半萜醇的重塑:氧定向氧化曼尼希反应的发现。
Org Lett. 2014 Feb 7;16(3):792-5. doi: 10.1021/ol4035269. Epub 2014 Jan 10.
2
Concise enantio- and diastereoselective total syntheses of fumagillol, RK-805, FR65814, ovalicin, and 5-demethylovalicin.烟曲霉素、RK-805、FR65814、椭圆玫瑰树碱和5-去甲基椭圆玫瑰树碱的简洁对映选择性和非对映选择性全合成。
Angew Chem Int Ed Engl. 2006 Jan 23;45(5):789-93. doi: 10.1002/anie.200502826.
3
Toward the Synthesis of Nuphar Sesquiterpene Thioalkaloids: Stereodivergent Rhodium-Catalyzed Synthesis of the Thiolane Subunit.迈向睡莲倍半萜硫代生物碱的合成:铑催化的硫杂环戊烷亚基的立体发散合成
J Org Chem. 2015 Aug 7;80(15):7581-9. doi: 10.1021/acs.joc.5b01177. Epub 2015 Jul 28.
4
A new, ring closing metathesis-based synthesis of (-)-fumagillol.
Org Lett. 2001 Aug 23;3(17):2737-40. doi: 10.1021/ol016343z.
5
Divergent total syntheses of (-)-lycopladine D, (+)-fawcettidine, and (+)-lycoposerramine Q.(-)-lycopladine D、(+)-fawcettidine 和 (+)-lycoposerramine Q 的发散全合成。
Org Lett. 2013 Nov 15;15(22):5846-9. doi: 10.1021/ol402906y. Epub 2013 Nov 4.
6
Syntheses of fumagillin and ovalicin.呋嘛精及卵形菌素的合成。
Chemistry. 2010 Apr 6;16(13):3884-901. doi: 10.1002/chem.200902433.
7
Remodelling of the natural product fumagillol employing a reaction discovery approach.采用反应发现方法对天然产物呋咱并[5,1-d]噻唑进行改造。
Nat Chem. 2011 Dec;3(12):969-73. doi: 10.1038/nchem.1178.
8
Design, synthesis, and antiangiogenic effects of a series of potent novel fumagillin analogues.一系列强效新型烟曲霉素类似物的设计、合成及抗血管生成作用
Chem Pharm Bull (Tokyo). 2007 Jul;55(7):1024-9. doi: 10.1248/cpb.55.1024.
9
An efficient total synthesis of (-)-huperzine A.(-)-石杉碱甲的高效全合成。
Org Lett. 2012 Sep 7;14(17):4446-9. doi: 10.1021/ol301951r. Epub 2012 Aug 17.
10
Stereoselective synthesis of oligo-alpha(2,8)-3-deoxy-D-manno-2-octulosonic acid derivatives.
Angew Chem Int Ed Engl. 2006 Jan 23;45(5):770-3. doi: 10.1002/anie.200503299.

引用本文的文献

1
Limonin as a Starting Point for the Construction of Compounds with High Scaffold Diversity.柚皮苷作为构建具有高支架多样性化合物的起点。
Angew Chem Int Ed Engl. 2021 Jul 12;60(29):16119-16128. doi: 10.1002/anie.202104228. Epub 2021 Jun 10.
2
Diversity-oriented synthesis of 17-spirosteroids.17-螺甾类化合物的多样性导向合成。
Beilstein J Org Chem. 2020 Apr 28;16:880-887. doi: 10.3762/bjoc.16.79. eCollection 2020.
3
Access to a Structurally Complex Compound Collection via Ring Distortion of the Alkaloid Sinomenine.通过阿片碱的环扭曲获得结构复杂的化合物库。

本文引用的文献

1
Natural products as starting points for the synthesis of complex and diverse compounds.天然产物作为合成复杂多样化合物的起点。
Nat Prod Rep. 2014 Jan;31(1):6-14. doi: 10.1039/c3np70063a.
2
Catalytic sp3 C-H oxidation of peptides and their analogues by radical cation salts: from glycine amides to quinolines.自由基阳离子盐促进的肽及其类似物的 sp3 C-H 氧化:从甘酰胺到喹啉。
J Org Chem. 2013 Sep 20;78(18):9450-6. doi: 10.1021/jo401018v. Epub 2013 Aug 28.
3
Iron-catalyzed oxidative tandem reactions with TEMPO oxoammonium salts: synthesis of dihydroquinazolines and quinolines.
Org Lett. 2016 Oct 7;18(19):4852-4855. doi: 10.1021/acs.orglett.6b02333. Epub 2016 Sep 21.
4
Rapid synthesis of polyprenylated acylphloroglucinol analogs via dearomative conjunctive allylic annulation.通过去芳构化共轭烯丙基环化快速合成多异戊烯基化酰基间苯三酚类似物。
J Am Chem Soc. 2014 Aug 20;136(33):11799-804. doi: 10.1021/ja5060302. Epub 2014 Aug 7.
5
Remodeling natural products: chemistry and serine hydrolase activity of a rocaglate-derived β-lactone.天然产物的改造:罗卡酯衍生的β-内酰胺的化学和丝氨酸水解酶活性。
J Am Chem Soc. 2014 Feb 12;136(6):2659-64. doi: 10.1021/ja412431g. Epub 2014 Feb 4.
铁催化的 TEMPO 氧铵盐氧化串联反应:二氢喹唑啉和喹啉的合成。
J Org Chem. 2013 Jun 21;78(12):6050-64. doi: 10.1021/jo4007199. Epub 2013 Jun 7.
4
Simultaneous structure-activity studies and arming of natural products by C-H amination reveal cellular targets of eupalmerin acetate.通过 C-H 胺化对天然产物进行同时的结构-活性研究和武装,揭示了醋酸橙花叔醇的细胞靶标。
Nat Chem. 2013 Jun;5(6):510-7. doi: 10.1038/nchem.1653. Epub 2013 May 19.
5
Iron-catalyzed oxidative C(3)-H functionalization of amines.铁催化的胺的 C(3)-H 氧化官能化。
Org Lett. 2013 Apr 19;15(8):1918-21. doi: 10.1021/ol400568u. Epub 2013 Apr 11.
6
Synthesis of skeletally diverse and stereochemically complex library templates derived from isosteviol and steviol.异甜菊醇和甜菊醇衍生的骨架多样和立体化学复杂文库模板的合成。
Org Lett. 2013 Apr 5;15(7):1602-5. doi: 10.1021/ol400385w. Epub 2013 Mar 26.
7
Translational synthetic chemistry.转化合成化学
Nat Chem Biol. 2013 Apr;9(4):210-3. doi: 10.1038/nchembio.1207.
8
A ring-distortion strategy to construct stereochemically complex and structurally diverse compounds from natural products.一种基于环扭曲策略的方法,可从天然产物中构建具有复杂立体化学和多样结构的化合物。
Nat Chem. 2013 Mar;5(3):195-202. doi: 10.1038/nchem.1549. Epub 2013 Jan 20.
9
Molecular library synthesis using complex substrates: expanding the framework of triterpenoids.利用复杂底物进行分子文库合成:扩大三萜类化合物的结构框架。
J Org Chem. 2013 Jan 18;78(2):410-8. doi: 10.1021/jo302211f. Epub 2013 Jan 10.
10
Scalable, enantioselective synthesis of germacrenes and related sesquiterpenes inspired by terpene cyclase phase logic.受萜烯环化酶相逻辑启发,可扩展的、对映选择性合成吉马烯及相关倍半萜。
Angew Chem Int Ed Engl. 2012 Nov 12;51(46):11491-5. doi: 10.1002/anie.201206904. Epub 2012 Oct 12.