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^*

^*Corresponding author for this work

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

12 Citations (Scopus)

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.

Original language	English
Pages (from-to)	6669-6678
Number of pages	10
Journal	Journal of Organic Chemistry
Volume	80
Issue number	13
DOIs	https://doi.org/10.1021/acs.joc.5b00836
Publication status	Published - 2015 Jul 2

ASJC Scopus subject areas

Organic Chemistry

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10.1021/acs.joc.5b00836

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title = "Biomimetic Approach toward the Total Synthesis of rac-2-(Acylmethylene)pyrrolidine Alkaloids",

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}",

note = "Publisher Copyright: {\textcopyright} 2015 American Chemical Society.",

year = "2015",

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

language = "English",

volume = "80",

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journal = "Journal of Organic Chemistry",

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T1 - Biomimetic Approach toward the Total Synthesis of rac-2-(Acylmethylene)pyrrolidine Alkaloids

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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DO - 10.1021/acs.joc.5b00836

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AN - SCOPUS:84942436831

SN - 0022-3263

VL - 80

SP - 6669

EP - 6678

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

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CCDC 1420487: Experimental Crystal Structure Determination

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

Abstract

ASJC Scopus subject areas

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CCDC 1420487: Experimental Crystal Structure Determination

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