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[利用有机金属配合物开发新的合成方法及其在天然产物合成中的应用]

[Development of new synthetic method using organometallic complexes and an application toward natural product synthesis].

作者信息

Mori Miwako

机构信息

Department of Fine Synthetic Chemistry, Graduate School of Pharmaceutical Sciences, Hokkaido University, Sapporo 060-0812, Japan.

出版信息

Yakugaku Zasshi. 2005 Jan;125(1):51-72. doi: 10.1248/yakushi.125.51.

DOI:10.1248/yakushi.125.51
PMID:15635281
Abstract

Recently, many organometallic complexes, such as palladium, nickel, ruthenium, titanium complexes and others, were used for synthetic organic chemistry. We have developed many novel synthetic methods using these organometallic complexes for synthetic organic chemistry. As the organometallic complexes, nickel, chromium, molybdenum, ruthenium, zirconium, titanium, and palladium complexes, were used. Furthermore, bimetallic complexes having silicon-tin and silicon-zirconium bonds were investigated. On the other hand, utilization of gases in synthetic organic chemistry has been also developed. 1 atm pressure of gases such as CO, CO(2), N(2), ethylene and acetylene, could be used and the reaction procedure is very simple, that a balloon filled with a gas is connected on the top of the flask. Using our novel synthetic methods, we have synthesized many natural products and biologically active substances, such as cephalotaxin, mesembrine, tubifoline, strychnine, stemoamide, lycopodine, pumiliotoxin C, beta-lactam, carbapenam and benzodiazepinone derivatives.

摘要

最近,许多有机金属配合物,如钯、镍、钌、钛配合物等,被用于有机合成化学。我们已经开发了许多使用这些有机金属配合物进行有机合成化学的新方法。作为有机金属配合物,使用了镍、铬、钼、钌、锆、钛和钯配合物。此外,还研究了具有硅-锡和硅-锆键的双金属配合物。另一方面,有机合成化学中气体的利用也得到了发展。可以使用1个大气压的气体,如CO、CO₂、N₂、乙烯和乙炔,反应过程非常简单,即将充满气体的气球连接在烧瓶顶部。使用我们的新合成方法,我们已经合成了许多天然产物和生物活性物质,如三尖杉酯碱、美登木碱、 tubifoline、士的宁、stemoamide、石松碱、箭毒蛙毒素C、β-内酰胺、碳青霉烯和苯二氮卓酮衍生物。

相似文献

1
[Development of new synthetic method using organometallic complexes and an application toward natural product synthesis].[利用有机金属配合物开发新的合成方法及其在天然产物合成中的应用]
Yakugaku Zasshi. 2005 Jan;125(1):51-72. doi: 10.1248/yakushi.125.51.
2
Collective synthesis of natural products by means of organocascade catalysis.通过有机级联催化对天然产物进行集体合成。
Nature. 2011 Jul 13;475(7355):183-8. doi: 10.1038/nature10232.
3
A novel and general synthetic pathway to strychnos indole alkaloids: total syntheses of (-)-tubifoline, (-)-dehydrotubifoline, and (-)-strychnine using palladium-catalyzed asymmetric allylic substitution.一种新颖且通用的士的宁吲哚生物碱合成途径:使用钯催化的不对称烯丙基取代反应全合成(-)-tubifoline、(-)-脱氢tubifoline和(-)-士的宁。
J Am Chem Soc. 2003 Aug 13;125(32):9801-7. doi: 10.1021/ja029382u.
4
[Development of new synthetic methods and their application to synthesis of useful compounds].[新型合成方法的开发及其在有用化合物合成中的应用]
Yakugaku Zasshi. 2003 Dec;123(12):1007-21. doi: 10.1248/yakushi.123.1007.
5
Novel synthesis of carbapenam by intramolecular attack of lactam nitrogen toward eta1-allenyl and eta3-propargylpalladium complex.
J Org Chem. 2003 Oct 17;68(21):8068-74. doi: 10.1021/jo030123c.
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Development of a novel synthetic method for ring construction using organometallic complexes and its application to the total syntheses of natural products.
Chem Pharm Bull (Tokyo). 2005 May;53(5):457-70. doi: 10.1248/cpb.53.457.
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An easy-to-use, regioselective, and robust bis(amidate) titanium hydroamination precatalyst: mechanistic and synthetic investigations toward the preparation of tetrahydroisoquinolines and benzoquinolizine alkaloids.
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[Synthesis of alkaloids using radical cyclizations].[利用自由基环化反应合成生物碱]
Yakugaku Zasshi. 2012;132(12):1413-30. doi: 10.1248/yakushi.12-00241.
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[Development of environmentally friendly organometallic catalysis for drug discovery and its application to heterocyclic chemistry].
Yakugaku Zasshi. 2007 Sep;127(9):1383-98. doi: 10.1248/yakushi.127.1383.
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Total Synthesis of Strychnine.士的宁的全合成。
Chemistry. 2017 Nov 16;23(64):16189-16193. doi: 10.1002/chem.201704455. Epub 2017 Oct 25.

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