Synthesis of the ABC-Ring System of the Azafluoranthene, Tropoisoquinoline and Proaporphine Alkaloids

Concise Synthesis of the ABC-Ring System of the Azafluoranthene, Tropoisoquinoline and Proaporphine Alkaloids: An Olefin Hydroacylation/Pomeranz–Fritsch Cyclization Approach: D. F. Vargas, E. L. Larghi, T. S. Kaufman
Synthesis 2019, DOI: 10.1055/s-0037-1611711


Biologically active alkaloids such as azafluoranthenes are contained in extracts of plants used for treating a variety of medical conditions in traditional medicine in South America. These compounds are structurally characterized by their unique indeno[1,2,3-ij]isoquinoline framework, which is shared by other bioactive alkaloids. The group of Professor T. S. Kaufman from the Universidad Nacional de Rosario (Argentina) recently reported a synthetic approach to the common tricyclic system of these alkaloids.

Professor Kaufman said: “We have developed a simple and efficient approach toward a cyclopenta[ij]isoquinoline derivative which embodies the ABC-ring system found in the azafluoranthene, tropoisoquinoline and proaporphine alkaloids. To that end, we combined a novel KF/Al2O3-mediated hydroacylation with a modified Pomeranz–Fritsch cyclization step. The approach may be useful for the synthesis of various natural products and technologically/pharmaceutically relevant compounds.”
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