A Stereodivergent Strategy for Total Syntheses of Antirhine Alkaloids

Eunjoon Park, Cheolwoo Bae, Cheon Gyu Cho, Cheol Hong Cheon

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2 Citations (Scopus)


Total syntheses of the antirhine alkaloids are described. The cyanide-catalyzed imino-Stetter reaction of the aldimine derived from ethyl 2-aminocinnamate and 4-bromopyridine-2-carboxaldehyde provided a 2-pyridinyl substituted indole-3-acetate, which was further converted into the corresponding indoloquinolizidinium intermediate through C-ring formation. Subsequent trans-selective installation of the homoallylic alcohol side-chain at C-15 in the resulting indoloquinolizidinium allowed the total syntheses of antirhine and its known epimer.

Original languageEnglish
Pages (from-to)4497-4511
Number of pages15
JournalJournal of Organic Chemistry
Issue number6
Publication statusPublished - 2021 Mar 19

Bibliographical note

Funding Information:
This work was supported by National Research Foundation of Korea (NRF) Grants funded by the Korean Government (NRF-2018R1D1A1A02086110 and NRF-2014-011165, Center for New Directions in Organic Synthesis).

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ASJC Scopus subject areas

  • Organic Chemistry


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