A Stereodivergent Strategy for Total Syntheses of Antirhine Alkaloids

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

Research output: Contribution to journalArticlepeer-review

1 Scopus citations

Abstract

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
Volume86
Issue number6
DOIs
StatePublished - 2021 Mar 19
Externally publishedYes

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