Concise Syntheses of bis-Strychnos Alkaloids (-)-Sungucine, (-)-Isosungucine, and (-)-Strychnogucine B from (-)-Strychnine

Zhao Senzhi; Teijaro Christiana N.; Chen Heng; Sirasani Gopal; Vaddypally Shivaiah; Zdilla Michael J.; Dobereiner Graham E.; Andrade Rodrigo B.

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Concise Syntheses of bis-Strychnos Alkaloids (-)-Sungucine, (-)-Isosungucine, and (-)-Strychnogucine B from (-)-Strychnine

机译：简明的双-Strychnos生物碱合成（-）-Strychnine（-）-Sungucine，（-）-Isosungucine和（-）-Strychnogucine B

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The first chemical syntheses of complex, bis-Strychnos alkaloids (-)-sungucine (1), (-)-isosungucine (2), and (-)-strychnogucine B (3) from (-)-strychnine (4) is reported. Key steps included (1) the Polonovski-Potier activation of strychnine N-oxide; (2) a biomimetic Mannich coupling to forge the signature C23-C5' bond that joins two monoterpene indole monomers; and (3) a sequential HBr/NaBH3CN-mediated reduction to fashion the ethylidene moieties in 1-3. DFT calculations were employed to rationalize the regiochemical course of reactions involving strychnine congeners.

机译：报道了从（-）-司氏碱（4）合成复杂的双-Strychnos生物碱（-）-sungucine（1），（-）-isosungucine（2）和（-）-strychnogucine B（3）的第一化学合成。。关键步骤包括：（1）士多宁N-氧化物的Polonovski-Potier活化; （2）仿生曼尼希偶合，以建立连接两个单萜吲哚单体的特征性C23-C5'键; （3）HBr / NaBH3CN介导的顺序还原，以形成1-3中的亚乙基部分。 DFT计算被用来合理化涉及士的宁同系物的反应的区域化学过程。

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《Chemistry: A European journal》 |2016年第33期|共4页
作者
Zhao Senzhi; Teijaro Christiana N.; Chen Heng; Sirasani Gopal; Vaddypally Shivaiah; Zdilla Michael J.; Dobereiner Graham E.; Andrade Rodrigo B.;
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正文语种 eng
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alkaloids; biomimetic synthesis; natural products; strychnine; sungucine;

机译：生物碱;仿生合成;天然产物;士土宁;升麻碱;

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1. Microstructure, Content and in vitro Release of Brucine and Strychnine in Strychnos Nux-Vomica Powder with Different Particle Sizes [J] . 倪力军, 赵雯雯, 张立国, 天津大学学报（英文版） . 2014,第006期
2. Concise Syntheses of bis-Strychnos Alkaloids (-)-Sungucine, (-)-Isosungucine, and (-)-Strychnogucine B from (-)-Strychnine [J] . Zhao Senzhi, Teijaro Christiana N., Chen Heng, Chemistry: A European journal . 2016,第33期

机译：简明的双-Strychnos生物碱合成（-）-Strychnine（-）-Sungucine，（-）-Isosungucine和（-）-Strychnogucine B
3. Apoptosis of HL-60 leukemia cells induced by the bisindole alkaloids sungucine and isosungucine from Strychnos icaja. [J] . Lansiaux A, Bailly C, Houssier C, Planta medica: Natural products and medicinal plant research . 2002,第7期

机译：美洲黑麦草的双吲哚生物碱sungucine和异双糖新碱诱导HL-60白血病细胞凋亡。
4. A Biomimetic Approach to the Strychnos Alkaloids. A Novel, Concise Synthesis of (±)-Akuamrnicine and a Route to (±)-Strychnine [J] . Stephen F. Martin, Cameron W. Clark, Masayuki Ito, Journal of the American Chemical Society . 1996,第40期

机译：马兜铃生物碱的仿生方法。（±）-Akuamrnicine的新颖，简洁的合成方法和（±）-Strychnine的途径。
5. Chemo-enzymatic rapid syntheses of tetrahydroisoquinoline alkaloids [C] . Ryo Tanifuji, Ryoko Komatsu, Takamitsu Honda 日本化学会春季年会講演予稿集 . 2018

机译：化学酶快速合成四氢异喹啉生物碱
6. Part I. A general, convergent strategy for the construction of indolizidine alkaloids: Total syntheses of (-)-indolizidine 223AB and alkaloid (-)-205B. Part II. Progress towards the total synthesis of spirastrellolide A: Preparation of the southern hemisphere [D] . Kim, Dae-Shik 2007

机译：第一部分：构建吲哚并立定生物碱的一般收敛策略：（-）-吲哚并立定223AB和生物碱（-）-205B的总合成。第二部分螺旋藻内酯全合成的进展A：南半球的制备
7. Concise Total Syntheses of the Lycopodium Alkaloids (±)-Nankakurines A and B via Luciduline [O] . Xiayun Cheng, Stephen P. Waters -1

机译：的石松生物碱的简明全合成（±）-Nankakurines a和经由Luciduline乙
8. Concise Syntheses of bis‐ Strychnos Alkaloids (−)‐Sungucine, (−)‐Isosungucine, and (−)‐Strychnogucine B from (−)‐Strychnine [O] . Senzhi Zhao, Christiana N. Teijaro, Heng Chen, 2016

机译：简洁的合成双 - strychnos生物碱（ - ） - sygucine，（ - ） - 异苏氨酸和（ - ） - 来自（ - ） - strychnine的strychnogine b

Concise Syntheses of bis-Strychnos Alkaloids (-)-Sungucine, (-)-Isosungucine, and (-)-Strychnogucine B from (-)-Strychnine

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