Asymmetric Total Syntheses of Mitragynine, Speciogynine, and 7-Hydroxymitragynine

A number of alkaloids found in Mitragyna species belonging to the Rubiaceae family have been shown to have potent biological activity such as analgesic properties. Here, we report the asymmetric total syntheses of mitragynine, speciogynine, and 7-hydroxymitragynine, which are classified as corynantheine-type monoter-penoid indole alkaloids, isolated from Mitragyna speciosa. These syntheses were accomplished within 12 steps and in > 11% total yield from commercial 3-(trimethylsilyl)propanal using an organocatalytic anti-selective Michael reaction and bioinspired transformations.

Automated summary

In this study, the total syntheses of several alkaloids from Mitragyna speciosa were successfully achieved using organocatalytic reactions and bioinspired transformations. These alkaloids exhibit potent biological activity with analgesic properties.