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Unified Total Synthesis of Five Gelsedine-Type Alkaloids: (−)-Gelsenicine, (−)-Gelsedine, (−)-Gelsedilam, (−)-14-Hydroxygelsenicine, and (−)-14,15-Dihydroxygelsenicine

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journal contribution
posted on 31.08.2016, 16:37 by Takaaki Harada, Jun Shimokawa, Tohru Fukuyama
The systematic arrangement of a two-carbon unit, hydrogen atom, and oxygen atom on the versatile enal moiety of a non-natural synthetic intermediate successfully led to the unified access to the gelsedine-type alkaloids. The development and use of this new synthetic hub and an array of site-selective transformations resulted in the asymmetric synthesis of (−)-gelsenicine, (−)-gelsedine, (−)-gelsedilam, (−)-14-hydroxygelsenicine, and (−)-14,15-dihydroxygelsenicine.