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

Department of Chemistry

Research output: Contribution to journal › Article

8 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

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ASJC Scopus subject areas

Organic Chemistry

Cite this

Shih, Y. C., Tsai, P. H., Hsu, C. C., Chang, C. W., Jhong, Y., Chen, Y. C., & Chien, T. C. (2015). Biomimetic Approach toward the Total Synthesis of rac-2-(Acylmethylene)pyrrolidine Alkaloids. Journal of Organic Chemistry, 80(13), 6669-6678. https://doi.org/10.1021/acs.joc.5b00836

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AU - Chen, Yun Chung

AU - Chien, Tun Cheng

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10.1021/acs.joc.5b00836