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

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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 languageEnglish
Pages (from-to)6669-6678
Number of pages10
JournalJournal of Organic Chemistry
Issue number13
Publication statusPublished - 2015 Jul 2


ASJC Scopus subject areas

  • Organic Chemistry

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