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Collective Asymmetric Total Synthesis of Cylindricines. 2023

Ryohei Hanzawa, and Haruhiko Fuwa
Department of Applied Chemistry, Faculty of Science and Engineering, Chuo University, 1-13-27 Kasuga, Bunkyo-ku, Tokyo 112-8551, Japan.

Collective asymmetric total synthesis of marine tricyclic alkaloids, cylindricines A-H, and the proposed structures of cylindricines I and J was achieved in a concise manner from a single common spirocyclic pyrrolidine intermediate. A tandem chemoselective oxidation/intramolecular aza-Michael addition/epimerization was exploited to complete the tricyclic skeleton. This work provides a versatile synthetic entry to the cylindricine family of marine tricyclic alkaloids.

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