Biomimetic Approach toward the Total Synthesis of rac-2-(Acylmethylene)pyrrolidine Alkaloids

Yu Chiao Shih; Pei Hua Tsai; Chia Chun Hsu; Chih Wei Chang; Yuandong Jhong; Yun Chung Chen; Tun Cheng Chien

doi:10.1021/acs.joc.5b00836

Biomimetic Approach toward the Total Synthesis of rac-2-(Acylmethylene)pyrrolidine Alkaloids

Yu Chiao Shih, Pei Hua Tsai, Chia Chun Hsu, Chih Wei Chang, Yuandong Jhong, Yun Chung Chen, Tun Cheng Chien^*

^*此作品的通信作者

化學系

研究成果: 雜誌貢獻 › 期刊論文 › 同行評審

12 引文斯高帕斯（Scopus）

摘要

2-(Acylmethylene)pyrrolidine derivatives were synthesized via intermolecular decarbonylative Mannich reaction from various methyl ketones and 1-alkyl-1-pyrroliniums, generated in situ from 1-alkylprolines. This approach mimics the biosynthetic pathway and provides a direct access to a series of 2-(acylmethylene)pyrrolidine alkaloids, including hygrine, N-methylruspolinone, dehydrodarlinine, and ruspolinone.

原文	英語
頁（從 - 到）	6669-6678
頁數	10
期刊	Journal of Organic Chemistry
卷	80
發行號	13
DOIs	https://doi.org/10.1021/acs.joc.5b00836
出版狀態	已發佈 - 2015 7月 2

ASJC Scopus subject areas

有機化學

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10.1021/acs.joc.5b00836

其它文件與鏈接

CCDC 1420487: Experimental Crystal Structure Determination
Shih, Y. (Creator), Tsai, P. (Creator), Hsu, C. (Creator), Chang, C. (Creator), Jhong, Y. (Creator), Chen, Y. (Creator) & Chien, T. (Creator), Unknown Publisher, 2015
DOI: 10.5517/cc1jp45j, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/cc1jp45j&sid=DataCite
資料集: Dataset

引用此

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abstract = "2-(Acylmethylene)pyrrolidine derivatives were synthesized via intermolecular decarbonylative Mannich reaction from various methyl ketones and 1-alkyl-1-pyrroliniums, generated in situ from 1-alkylprolines. This approach mimics the biosynthetic pathway and provides a direct access to a series of 2-(acylmethylene)pyrrolidine alkaloids, including hygrine, N-methylruspolinone, dehydrodarlinine, and ruspolinone.",

author = "Shih, {Yu Chiao} and Tsai, {Pei Hua} and Hsu, {Chia Chun} and Chang, {Chih Wei} and Yuandong Jhong and Chen, {Yun Chung} and Chien, {Tun Cheng}",

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doi = "10.1021/acs.joc.5b00836",

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AU - Shih, Yu Chiao

AU - Tsai, Pei Hua

AU - Hsu, Chia Chun

AU - Chang, Chih Wei

AU - Jhong, Yuandong

AU - Chen, Yun Chung

AU - Chien, Tun Cheng

PY - 2015/7/2

Y1 - 2015/7/2

N2 - 2-(Acylmethylene)pyrrolidine derivatives were synthesized via intermolecular decarbonylative Mannich reaction from various methyl ketones and 1-alkyl-1-pyrroliniums, generated in situ from 1-alkylprolines. This approach mimics the biosynthetic pathway and provides a direct access to a series of 2-(acylmethylene)pyrrolidine alkaloids, including hygrine, N-methylruspolinone, dehydrodarlinine, and ruspolinone.

AB - 2-(Acylmethylene)pyrrolidine derivatives were synthesized via intermolecular decarbonylative Mannich reaction from various methyl ketones and 1-alkyl-1-pyrroliniums, generated in situ from 1-alkylprolines. This approach mimics the biosynthetic pathway and provides a direct access to a series of 2-(acylmethylene)pyrrolidine alkaloids, including hygrine, N-methylruspolinone, dehydrodarlinine, and ruspolinone.

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JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 13

ER -

Biomimetic Approach toward the Total Synthesis of rac-2-(Acylmethylene)pyrrolidine Alkaloids

摘要

ASJC Scopus subject areas

存取文件

其它文件與鏈接

指紋

資料集

CCDC 1420487: Experimental Crystal Structure Determination

引用此