Asymmetric Total Syntheses of Mitragynine, Speciogynine, and 7-Hydroxymitragynine
Jukiya Sakamoto, Mariko Kitajima, Hayato Ishikawa
Abstract
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 monoterpenoid 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.
Topics & Concepts
ChemistryTotal synthesisRubiaceaeStereochemistryIndole testYield (engineering)Traditional medicineBotanyBiologyMetallurgyMedicineMaterials scienceAlkaloids: synthesis and pharmacologyTraditional and Medicinal Uses of AnnonaceaeChemical synthesis and alkaloids