Synthesis of the tricyclic core of manzamine A?

Organic & Biomolecular Chemistry Pub Date: 2015-01-27 DOI: 10.1039/C4OB02582B

Abstract

An efficient synthetic approach to the core structure of the manzamine alkaloids is reported, particularly in relation to incorporating a one-carbon unit in ring B from which the aldehyde in ircinal A or the beta-carboline unit in manzamine A could potentially be generated. The key steps involve a Johnson–Claisen rearrangement, enolate alkylation, dithiane alkylation and a stereoselective intramolecular dipolar cycloaddition of an azomethine ylide, which provided the desired tricyclic ABC core structure.

Graphical abstract: Synthesis of the tricyclic core of manzamine A
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