Approaches to the Synthesis of Manzamine A. Synthesis of the SS-Carboline-Bearing Abce Ring System (original) (raw)

1995, Heterocyclic Communications

The 8-membered ring Ε has been introduced onto a strategically functionalized chiral pyrrolo[2,3-/]isoquinoline derivative by a combination of a Wittig coupling and amide cyclization. The resulting tetracyclic structure has been converted to the ABCE-ß-carboline ring system of manzamine A. The novel structure and significant biological activity of manzamine A 1-an alkaloid isolated from sea sponges found in the Okinawan waters (1)-has drawn keen attention in connection with its biosynthetic origin (2) and chemical synthesis (3). In a retrosynthetic analysis of the alkaloid, we, and a number of other groups, have recognized that the ABC ring system of manzamine A constitutes a core structure upon which the remaining rings of the target compound may be elaborated. In this context, we reported the first synthesis of the strategically functionalized chiral pyrrolo[2,3-/]isoquinoline intermediate 2 (3d). We now present the elaboration of 2 to the ABCE-ß-carboline ring system of manzamine A.

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