Synthesis of Bicyclic Proline Derivatives by the Aza-Cope-Mannich Reaction: Formal Synthesis of (+/-)-Acetylaranotin

Belov Dmitry S.; Ratmanova Nina K.; Andreev Ivan A.; Kurkin Alexander V.

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Synthesis of Bicyclic Proline Derivatives by the Aza-Cope-Mannich Reaction: Formal Synthesis of (+/-)-Acetylaranotin

机译：通过Aza-Cope-Mannich反应合成双环脯氨酸衍生物：（+/-）-乙酰天青素的形式合成

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Herein we suggest an approach to oxygenated bicyclic amino acids based on an aza-Cope-Mannich rearrangement. Seven distinct amino acid scaffolds analogous to the natural products were prepared on a gram scale with precise control of stereochemistry. Successful implementation of our strategy resulted in the formal synthesis of acetylaranotin.

机译：本文中，我们提出了一种基于aza-Cope-Mannich重排的氧化双环氨基酸的方法。在精确控制立体化学的情况下，以克为标准制备了七个与天然产物相似的独特氨基酸支架。成功实施我们的策略导致了正式合成乙酰阿拉伯糖苷。

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《Chemistry: A European journal》 |2015年第10期|共7页
作者
Belov Dmitry S.; Ratmanova Nina K.; Andreev Ivan A.; Kurkin Alexander V.;
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正文语种 eng
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amino acids; medicinal chemistry; natural products; rearrangement; total synthesis;

机译：氨基酸;药物化学;天然产物;重排;全合成;

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1. Synthesis of Bicyclic Proline Derivatives by the Aza-Cope-Mannich Reaction: Formal Synthesis of (+/-)-Acetylaranotin [J] . Belov Dmitry S., Ratmanova Nina K., Andreev Ivan A., Chemistry: A European journal . 2015,第10期

机译：通过Aza-Cope-Mannich反应合成双环脯氨酸衍生物：（+/-）-乙酰天青素的形式合成
2. Synthesis of Bicyclic Proline Analogs Using a Formal [3 + 2] Intramolecular Aziridine-Allylsilane Cycloaddition Reaction [J] . Stephen C. Bergmeier, Susan L. Fundy, Punit P. Seth Tetrahedron . 1999,第26期

机译：使用形式的[3 + 2]分子内氮丙啶-烯丙基硅烷环加成反应合成双环脯氨酸类似物
3. Formal Asymmetric Synthesis of Pentalenolactone E and Pentalenolactone F 1. Retrosynthesis and π-Facial Differentiation in Palladium-Catalyzed and Dipolar [3 + 2]-Cycloaddition Reactions of Bicyclic Alkenes: Evidence for Electrostatic Control of Ste [J] . Bernd Rosenstock, Hans-Joachim Gais, Eva Herrmann, European journal of organic chemistry . 1998,第2期

机译：戊烯内酯E和戊烯内酯F的形式不对称合成1.双环烯烃在钯催化和偶极[3 + 2]-环加成反应中的反合成和π相分化：静电控制Ste的证据
4. Synthesis and Biological Activity of Novel a-Conotoxin Analogues Incorporating Substituted Proline Derivatives [C] . Christopher J. Armishaw, Anders A. Jensen, Christian Skonberg American Peptide Symposium . 2009

机译：一种掺入脯氨酸衍生物的新型A-Conotoxin类似物的合成和生物活性
5. Part I. Asymmetric organocatalysis: (1) Direct enantioselective organocatalytic hydroxymethylation of aldehydes catalyzed by alpha,alpha-diphenylprolinol trimethylsilyl ether: Application in the formal synthesis of (-)-Rasfonin; (2) Synthesis of a novel bicyclic secondary amine organocatalyst: Application to the direct enantioselective organocatalytic hydroxymethylation of aldehydes. Part II. Asymmetric synthesis of bicyclic analogues of the anti-osteoporotic drug risedronate. [D] . Miller, John Robert. 2010

机译：第一部分，不对称有机催化：（1）α，α-二苯基脯氨醇三甲基甲硅烷基醚催化的醛的直接对映选择性有机催化羟甲基化：在（-）-Rasfonin的正式合成中的应用；（2）新型双环仲胺有机催化剂的合成：应用于醛的直接对映选择性有机催化羟甲基化。第二部分抗骨质疏松药物Risedronate的双环类似物的不对称合成。
6. A Mild Synthesis of Bicyclic Alkoxyoxazolium Salts from Proline and Pipecolic Acid Derivatives [O] . Eleonora Spinozzi, Adriano Bauer, Nuno Maulide -1

机译：从脯氨酸和胡椒酸衍生物轻度合成双环烷恶唑盐。
7. A Mild Synthesis of Bicyclic Alkoxyoxazolium Salts from Proline and Pipecolic Acid Derivatives [O] . Eleonora Spinozzi, Adriano Bauer, Nuno Maulide 2019

机译：来自脯氨酸和苯乙烯酸衍生物的双环烷氧基毒碱盐的温和合成

Synthesis of Bicyclic Proline Derivatives by the Aza-Cope-Mannich Reaction: Formal Synthesis of (+/-)-Acetylaranotin

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