Total Synthesis of Benzo[c]phenanthridine Alkaloids, Chelerythrine and 12-Methoxydihydrochelerythrine,by a Palladium-Assisted Internal Biaryl Coupling Reaction

Takashi Harayama; TOshihiko Akiyama; Hisashi Akamatsu; Kazuko Kawano; Hitoshi Abe; Yasuo Takeuchi

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Total Synthesis of Benzo[c]phenanthridine Alkaloids, Chelerythrine and 12-Methoxydihydrochelerythrine,by a Palladium-Assisted Internal Biaryl Coupling Reaction

机译：钯辅助内部联芳基偶联反应的全合成苯并[c]菲啶生物碱，白屈菜红碱和12-甲氧基二氢白屈菜红碱

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摘要

A covenient and versatile synthesis of benzo[c]phenanthrrding alkaloids,chelerythrine (1) and 12-mehtoxydihydrochelerythrine (5),was accomplished via an internal aryl-aryl coupling reaction of haloamides 8 and 9 by a palladium-assisted cyclization reaction.

机译：通过钯辅助环化反应，通过卤代酰胺8和9的内部芳基-芳基偶联反应，完成了苯并[c]菲生物碱，白屈菜红碱（1）和12-甲氧基二氢白屈菜红碱（5）的简便，通用合成。

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《Synthesis: International Journal of Methods in Synthetic Organic Chemistry》 |2001年第3期|共7页
作者
Takashi Harayama; TOshihiko Akiyama; Hisashi Akamatsu; Kazuko Kawano; Hitoshi Abe; Yasuo Takeuchi;
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正文语种 eng
中图分类有机化学;
关键词
alkaloids; internal aryl-aryl coupling; ring closure; heck-type reaction; palladium; haloamides;

机译：生物碱;内部芳基-芳基偶联;闭环;颈型反应;钯;卤代酰胺;

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1. Total Synthesis of Benzo[c]phenanthridine Alkaloids, Chelerythrine and 12-Methoxydihydrochelerythrine,by a Palladium-Assisted Internal Biaryl Coupling Reaction [J] . Takashi Harayama, TOshihiko Akiyama, Hisashi Akamatsu, Synthesis: International Journal of Methods in Synthetic Organic Chemistry . 2001,第3期

机译：钯辅助内部联芳基偶联反应的全合成苯并[c]菲啶生物碱，白屈菜红碱和12-甲氧基二氢白屈菜红碱
2. Concise synthesis of fagaridine and decarine, phenolic benzo[c]phenanthridine alkaloids, using the palladium-assisted biaryl coupling reaction [J] . Takashi Harayama, Tomonori Sato, Yuichiro Nakano, Heterocycles: An International Journal for Reviews and Communications in Heterocyclic Chemistry . 2003,第1期

机译：钯辅助联芳基偶联反应可轻松合成法加替丁和十氢萘，酚类苯并[c]菲啶生物碱
3. Palladium-catalyzed tandem reaction to construct benzo[c]phenanthridine:application to the total synthesis of benzo[c]phenanthridine alkaloids [J] . Pei Lv, Kanglun Huang, Longguan Xie, Organic & biomolecular chemistry . 2011,第9期

机译：钯催化串联反应构建苯并[c]菲啶：在全合成苯并[c]菲啶生物碱中的应用
4. Biaryl Cross-Coupling Reactions Controlled by Fluoride Ion and Bulky Monodentate Ligands [C] . Takuji Hatakeyama, Sigma Hashimoto, Kentarb Ishizuka Symposium on Organometallic Chemistry . 2008

机译：由氟离子和庞大的单齿配体控制的Biaryl交叉偶联反应
5. An application of the intramolecular Heck reaction: A new strategy in the synthesis of Hasubanan alkaloids. Preparation of unsymmetrical biaryls via the Stille cross-coupling reaction: Synthesis of highly functional intermediates towards the synthesis of vindoline. [D] . Frank, Anthony Joseph. 2002

机译：分子内Heck反应的应用：合成Hasubanan生物碱的新策略。通过Stille交叉偶联反应制备不对称的联芳基：合成高功能性中间体，合成长春新碱。
6. Total Synthesis of Chiral Biaryl Natural Products by Asymmetric Biaryl Coupling [O] . Marisa C. Kozlowski, Barbara J. Morgan, Elizabeth C. Linton -1

机译：通过不对称联芳耦合手性联芳天然产物的全合成
7. A Convenient Synthesis of Benzo(c)phenanthridine Alkaloid, Chelerythrine, by the Palladium-Assisted Internal Biaryl Coupling Reaction. [O] . Takashi HARAYAMA, Toshihiko AKIYAMA, Kazuko KAWANO 1996

机译：方便合成苯并（C）菲啶生物碱，Chelerythrine，通过钯辅助内部辅导芳基偶联反应。

Total Synthesis of Benzo[c]phenanthridine Alkaloids, Chelerythrine and 12-Methoxydihydrochelerythrine,by a Palladium-Assisted Internal Biaryl Coupling Reaction

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