Synthesis of L-6-chloropyrroloindoline of chloptosin cyclohexapeptide

Abstract

Chloptosin is an apoptosis-inducing dimeric cyclohexapeptide. Enantio-selective synthesis of L-6-chloropyrroloindoline, as the key chiral synthon of the cyclohexapeptide of chloptosin, was successfully achieved starting from 3-chloroaniline by utilizing Fischer indole/Schöllkopf protocol and oxidative cyclization of resulting L-6-chlorotryptophan.