Synthetic studies of decursivine derivatives: preparation of key indole alkaloids via α-hydroxyalkylation

2-Hydroxyacetyl indole modified at C-3 position was prepared with an eye to developing a total synthesis of decursivine derivatives (decursivine, serotobenine, moschaminindolol, and flavumindole). The indole was prepared through a sequence of oxalyl chloride introduction at C-3 position of indole and acid chloride reduction with tributyltin hydride. In addition, we report a novel synthesis of fully functionalized Uhle's ketone via ortho-selective α-hydroxyalkylation.

Graphical abstractDownload full-size image