A Platform for the Synthesis of Corynantheine-Type Corynanthe Alkaloids

Yunchan Nam, Anthony T. Tam, Eric R. Miller, Karl A. Scheidt*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

1 Scopus citations

Abstract

Corynantheine-type alkaloids are major components of the Mitragyna speciosa, also known as kratom, that exhibit unique pharmacological activity. However, no universal method to prepare these alkaloids has been reported. Disclosed herein is a catalytic, asymmetric platform that enables rapid access to corynantheine alkaloids. The first enantioselective total synthesis of (−)-corynantheidine pseudoindoxyl is described. The first asymmetric syntheses of (+)-corynoxine and (−)-corynoxine B were also achieved, along with enantioselective syntheses of (−)-corynantheidol and (−)-corynantheidine. Through this work, all series of corynantheine alkaloids including indole, spirooxindole, and pseudoindoxyl can now be accessed in the laboratory, enabling comprehensive biological investigation of kratom alkaloids to be undertaken.

Original languageEnglish (US)
Pages (from-to)118-124
Number of pages7
JournalJournal of the American Chemical Society
Volume146
Issue number1
DOIs
StatePublished - Jan 10 2024

ASJC Scopus subject areas

  • General Chemistry
  • Biochemistry
  • Catalysis
  • Colloid and Surface Chemistry

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