A Concise Synthesis of Isocryptolepine by C–C Cross-Coupling Followed by a Tandem C–H Activation and C–N Bond FormationThe University of Stavanger Toppforsk program and the research program Bioactive is acknowledged for financial support of the study.
Received: 02 June 2017
Accepted: 06 June 2017
27 June 2017 (online)
Isocryptolepine (1), a potent antimalarial natural product, was prepared in three steps from 3-bromoquinoline and 2-aminophenylboronic acid hydrochloride. The key transformations were a Suzuki–Miyaura cross-coupling reaction followed by a palladium-initiated intramolecular C–H activation/C–N bond formation between an unprotected amine and an aromatic C–H group. The two key reactions can also be performed in one pot.