Collective Total Synthesis of β-Carboline-Type Monoterpenoid Indole Alkaloid Glycosides

The collective and efficient asymmetric total syntheses of five beta-carboline-type monoterpenoid indole alkaloid glycosides were achieved in fewer than thirteen steps. A Pictet-Spengler reaction with alpha-cyanotryptamine followed by the removal of the cyano group and autoxidation (aromatization) efficiently constructed the beta-carboline motif. In addition, bioinspired reactions were developed to provide different alkaloid skeletons.

Automated summary

In this study, the collective and efficient asymmetric total syntheses of five beta-carboline-type monoterpenoid indole alkaloid glycosides were successfully achieved in fewer than thirteen steps. The beta-carboline motif was efficiently constructed through a Pictet-Spengler reaction with alpha-cyanotryptamine, followed by the removal of the cyano group and autoxidation (aromatization). Furthermore, bioinspired reactions were developed to provide different alkaloid skeletons.