A Platform for the Synthesis of Corynantheine-Type Corynanthe Alkaloids

A Platform for the Synthesis of Corynantheine-Type Corynanthe Alkaloids

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 t...

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Veröffentlicht in:Journal of the American Chemical Society 2024-01, Vol.146 (1), p.118-124
Hauptverfasser: Nam, Yunchan, Tam, Anthony T., Miller, Eric R., Scheidt, Karl A.
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container_title Journal of the American Chemical Society
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creator Nam, Yunchan
Tam, Anthony T.
Miller, Eric R.
Scheidt, Karl A.
description 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.
doi_str_mv 10.1021/jacs.3c12556
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title A Platform for the Synthesis of Corynantheine-Type Corynanthe Alkaloids
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