First stereospecific total synthesis of (-)-affinisine oxindole as well as facile entry into the C(7)-diastereomeric chitosenine stereochemistry

Fonseca German O.; Wang Zhi-Jian; Namjoshi Ojas A.; Deschamps Jeffrey R.; Cook James M.

首页> 外文期刊>Tetrahedron letters: The International Journal for the Rapid Publication of Preliminary Communications in Organic Chemistry >First stereospecific total synthesis of (-)-affinisine oxindole as well as facile entry into the C(7)-diastereomeric chitosenine stereochemistry

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First stereospecific total synthesis of (-)-affinisine oxindole as well as facile entry into the C(7)-diastereomeric chitosenine stereochemistry

机译：（-）-Affinisine oxindole的第一个立体有针对性的全合成以及容易进入C（7）-非对映异构的几丁质立体化学

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The first synthesis of (-)-affinisine oxindole was completed in an enantiospecific fashion from commercially available D-(+)-tryptophan in 10% overall yield. The asymmetric Pictet-Spengler reaction, diastereo-specific oxidative-rearrangement of a tetrahydro-beta-carboline, and stereospecific enolate-mediated palladium-catalyzed cross coupling process were key steps in the sequence. This represents the first example of a total synthesis via stereospecific entry into either the alstonisine related or epimeric chitosenine related oxindole stereochemistry depending on the presence or absence of an N-b-benzyl protecting group. (C) 2014 Elsevier Ltd. All rights reserved.

机译：（-）-Affinisine oxindole的首次合成以对映体特异性方式从市售D-（+）-色氨酸以10％的总产率完成。该序列的关键步骤是不对称的Pictet-Spengler反应，非对映特异性氧化重排的四氢β-咔啉和立体定向烯醇化物介导的钯催化的交叉偶联过程。这代表了根据存在或不存在N-b-苄基保护基，通过立体定向进入与阿尔斯通相关的或与差向异构的几丁氨酸相关的羟吲哚立体化学的总合成的第一个例子。（C）2014 Elsevier Ltd.保留所有权利。

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《Tetrahedron letters: The International Journal for the Rapid Publication of Preliminary Communications in Organic Chemistry》 |2015年第23期|共5页
作者
Fonseca German O.; Wang Zhi-Jian; Namjoshi Ojas A.; Deschamps Jeffrey R.; Cook James M.;
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正文语种 eng
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Affinisine oxindole; Oxindoles; Oxindole-rearrangement; Palladium-catalyzed cross coupling; Tetrahydro-beta-carbolines;

机译：Affinisine oxindole;Oxindoles;Oxindole重排;钯催化的交叉偶联;四氢β-咔啉;

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1. First stereospecific total synthesis of (-)-affinisine oxindole as well as facile entry into the C(7)-diastereomeric chitosenine stereochemistry [J] . Fonseca German O., Wang Zhi-Jian, Namjoshi Ojas A., Tetrahedron letters: The International Journal for the Rapid Publication of Preliminary Communications in Organic Chemistry . 2015,第23期

机译：（-）-Affinisine oxindole的第一个立体有针对性的全合成以及容易进入C（7）-非对映异构的几丁质立体化学
2. First Asymmetric Total Synthesis of Us-7 and -8, Novel D-seco Corynanthe-Type Oxindole Alkaloids from Uncaria attenuata: Structure Revision of Us-7 and Determination of Absolute Stereochemistry [J] . Hiromitsu Takayama, Rika Fujiwara, Yasuko Kasai, Organic letters . 2003,第16期

机译：US-7和-8的首次不对称全合成，新的D-seco Corynanthe型氧化吲哚生物碱，由无毒钩藤制成：Us-7的结构修饰和绝对立体化学的确定
3. Stereospecific Total Synthesis of the Indole Alkaloid Ervincidine. Establishment of the C?6 Hydroxyl Stereochemistry [J] . Sundari K. Rallapalli, Ojas A. Namjoshi, V. V. N. Phani Babu Tiruveedhula, The Journal of Organic Chemistry . 2014,第9期

机译：吲哚生物碱二硅烷的立体尺寸全合成。建立C？6羟基立体化学
4. A Novel Reductive N-Alkylation in a Triruthenium Carbonyl Cluster-Catalyzed Reduction of Secondary Amides with Polymethylhydrosiloxane:A New Entry to the Facile Synthesis of Tertiary Amines [C] . Yukihiro Motoyama, Toshiki Ishida, Shiori Hanada Symposium on Organometallic Chemistry . 2006

机译：用聚甲基氢硅氧烷的三rruthenium羰基簇催化还原仲酰胺的新型还原N-烷基化：第三胺的体内合成的新进入
5. Enantiospecific stereospecific strategy for the total synthesis of sarpagine and macroline related oxindole alkaloids: First total synthesis of affinisine oxindole, isoalstonisine, alstofoline, macrogentine, N(1)-demethylalstonisine, alstonoxine a and second generation synthesis of alstonisine. [D] . Fonseca Cabrera, German Oscar. 2015

机译：对映体立体定向策略，用于总合成沙雷平和大分子相关的羟吲哚生物碱：仿制药的羟吲哚，异alstonisine，alstofoline，macrogentine，N（1）-去甲基阿司他丁，alstonoxine a的第二次总合成以及alstonisine的第二代合成。
6. Concise Total Synthesis of (−)-Affinisine Oxindole (+)-Isoalstonisine (+)-Alstofoline (−)-Macrogentine (+)-Na-Demethylalstonisine (−)-Alstonoxine A and (+)-Alstonisine [O] . Michael Rajesh Stephen, M. Toufiqur Rahman, V.V.N. Phani Babu Tiruveedhula, -1

机译：（-）-Affinisine Oxindole（+）-Isoalstonisine（+）-Alstofoline（-）-Macrogentine（+）-Na-Demethylalstonisine（-）-Alstonoxine A和（+）-Alstonisine的简明全合成
7. Concise Total Synthesis of (−)-Affinisine Oxindole, (+)-Isoalstonisine, (+)-Alstofoline, (−)-Macrogentine, (+)-N a -Demethylalstonisine, (−)-Alstonoxine A, and (+)-Alstonisine [O] . Michael Rajesh Stephen, M. Toufiqur Rahman, V. V. N. Phani Babu Tiruveedhula, 2017

机译：简化的总合成（ - ） - 酰胺氧吲哚，（+） - 异戊酮，（+） - 阿尔替氟醇，（ - ） - 宏酮，（+） - N A -Demethylstonisine，（ - ） - 阿尔斯酮胺A和（+） - 阿尔斯隆西丁
8. Total Synthesis of Isopavine and Intermediates for the Preparation of Substituted Amitriptyline Analogues: Facile Routes to Substituted Dibenzocyclooctatrienes and Dibenzocycloheptatrienes [R] . Jung, M. E., Miller, S. J. 1980

机译：用于制备取代的阿米替林类似物的异哌嗪和中间体的全合成：取代的二苯并环辛三烯和二苯并环庚三烯的简易途径

First stereospecific total synthesis of (-)-affinisine oxindole as well as facile entry into the C(7)-diastereomeric chitosenine stereochemistry

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