Organocatalytic Highly Enantioselective Substitution of 3-(1-Tosylalkyl)indoles with Oxindoles Enables the First Total Synthesis of (+)-Trigolutes B

Huang Jian-Zhou; Zhang Chen-Long; Zhu Yi-Fan; Li Lu-Lu; Chen Dian-Feng; Han Zhi-Yong; Gong Liu-Zhu

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Organocatalytic Highly Enantioselective Substitution of 3-(1-Tosylalkyl)indoles with Oxindoles Enables the First Total Synthesis of (+)-Trigolutes B

机译：3-（1-甲苯磺酰基烷基）吲哚与吲哚的有机催化高度对映选择性可实现（+）-Trigolutes B的首次全合成

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A highly enantioselective organocatalytic substitution of 3-(1-tosylalkyl)indoles with oxindoles has been established by using chiral bifunctional organocatalysts, providing an efficient entry to multiply functionalized 3,3-disubstituted oxindoles, and was exploited as the key step to enable the first asymmetric total synthesis of optically pure (+)-trigolutesB to be accomplished in a concise manner, within seven steps with an 18% overall yield.

机译：通过使用手性双官能有机催化剂已经建立了3-（1-甲苯磺酰基烷基）吲哚对映体的高度对映选择性有机催化，为多官能化的3,3-二取代的羟吲哚提供了有效的入口，并被用作实现第一个第一步的关键步骤。以简明的方式在七个步骤内完成光学纯（+）-trigolutesB的不对称总合成，总产率为18％。

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《Chemistry: A European journal》 |2015年第23期|共5页
作者
Huang Jian-Zhou; Zhang Chen-Long; Zhu Yi-Fan; Li Lu-Lu; Chen Dian-Feng; Han Zhi-Yong; Gong Liu-Zhu;
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正文语种 eng
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关键词
asymmetric synthesis; enantioselectivity; organocatalysis; spirooxindoles; total synthesis;

机译：不对称合成;对映选择性;有机催化;螺硫醇;全合成;

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1. Organocatalytic Highly Enantioselective Substitution of 3-(1-Tosylalkyl)indoles with Oxindoles Enables the First Total Synthesis of (+)-Trigolutes B [J] . Huang Jian-Zhou, Zhang Chen-Long, Zhu Yi-Fan, Chemistry: A European journal . 2015,第23期

机译：3-（1-甲苯磺酰基烷基）吲哚与吲哚的有机催化高度对映选择性可实现（+）-Trigolutes B的首次全合成
2. Highly enantioselective synthesis of 3-amino-2-oxindole derivatives: Catalytic asymmetric α-amlnation of 3-substituted 2-oxindoles with a chiral scandium complex [J] . Yang Z., Wang Z., Bai S., Chemistry: A European journal . 2010,第22期

机译：3-氨基-2-氧吲哚衍生物的高度对映选择性合成：3-取代的2-氧吲哚与手性scan配合物的催化不对称α-接枝
3. Highly Enantioselective Synthesis of 3-Amino-2-oxindole Derivatives: Catalytic Asymmetric -Amination of 3-Substituted 2-Oxindoles with a Chiral Scandium Complex [J] . Zhigang Yang Zhen Wang Sha Bai Ke Shen Donghui Chen Xiaohua Liu Dr. Lili Lin Dr. Xiaoming Feng Prof. Dr. Chemistry - A European Journal . 2010,第22期

机译：3-氨基-2-氧吲哚衍生物的高度对映选择性合成：手性Scan络合物催化3位取代的2-Oxindoles的催化不对称胺化
4. Enantioselective Organocatalytic Cascade Reaction for the Asymmetric Synthesis of Poly substituted Furofuranes [C] . Efraim Reyes, Garazi Talavera, Jose L. Vicario European Symposium on Organic Chemistry . 2009

机译：对聚取代呋喃脲的不对称合成的对映选择性有机催化级联反应
5. Part I. General approach to the total synthesis of 9-methoxy substituted indole alkaloids: Total synthesis of the opioid agonistic indole alkaloid, mitragynine as well as 9-methoxy-geissoschizol and 9-methoxy-N(b)-methylgeissoschizol. Part II. Studies toward the total synthesis of the antimalarial bisindole alkaloid villastonine. [D] . Ma, Jun. 2006

机译：第一部分。9-甲氧基取代的吲哚生物碱的总合成的一般方法：阿片类激动剂吲哚生物碱，米塔吉宁以及9-甲氧基-Geissoschizol和9-甲氧基-N（b）-甲基Geissoschizol的总合成。第二部分对抗疟药双吲哚生物碱坏死精的全合成的研究。
6. Organocatalytic Highly Enantioselective Tandem Michael-Knoevenagel Reaction for the Synthesis of Substituted Thiochromanes [O] . Rajasekhar Dodda, Tanmay Mandal, Cong-Gui Zhao -1

机译：有机催化高对映选择性串联Michael-Knoevenagel反应合成取代的硫代色烷
7. Organocatalytic highly enantioselective tandem Michael–Knoevenagel reaction for the synthesis of substituted thiochromanes [O] . Rajasekhar Dodda, Tanmay Mandal, Cong-Gui Zhao 2008

机译：有机催化高度对映选择性的串联迈克尔 - 朗格那雷加反应，用于合成取代的硫化体

Organocatalytic Highly Enantioselective Substitution of 3-(1-Tosylalkyl)indoles with Oxindoles Enables the First Total Synthesis of (+)-Trigolutes B

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