CC BY ND NC 4.0 · SynOpen 2017; 01(01): 0041-0044
DOI: 10.1055/s-0036-1590807
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A Concise Synthesis of Isocryptolepine by C–C Cross-Coupling Followed by a Tandem C–H Activation and C–N Bond Formation

Ida T. Urdal Helgeland, Magne O. Sydnes*
  • Faculty of Science and Technology, Department of Mathematics and Natural Science, University of Stavanger, 4036 Stavanger, Norway   Email: magne.o.sydnes@uis.no
The University of Stavanger Toppforsk program and the research program Bioactive is acknowledged for financial support of the study.
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Publication History

Received: 02 June 2017

Accepted: 06 June 2017

Publication Date:
27 June 2017 (online)

Abstract

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.

Supporting Information