The Asymmetric Total Synthesis of Discorhabdin B, H, K, and Aleutianamine

Abstract

AbstractThis review article summarizes the general introduction of discorhabdin marine alkaloids and the synthetic efforts in developing congeners with a hexacyclic N, S-acetal structure, which are major constituents of discorhabdin. Our total synthesis of (+)-discorhabdin B is discussed in detail following the introduction of the biosynthetic pathway and early synthetic studies, which include the landmark first total synthesis of discorhabdin A. Furthermore, previous synthetic studies on more structurally complex congeners with C6–N15 bonds are introduced, followed by the first total synthesis of (–)-discorhabdin H and (+)-discorhabdin K, which are achieved by our research group. Finally, the isolation, structure determination, and proposed biosynthesis of the structurally intriguing congener aleutianamine are summarized. Then, the first total synthesis of aleutianamine, which involves an unprecedented reductive skeletal rearrangement of N-Ts-(+)-discorhabdin B to N-Ts-aleutianamine, is discussed.