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Issue 11, 2015
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Synthesis of the tricyclic core of manzamine A

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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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Publication details

The article was received on 10 Dec 2014, accepted on 27 Jan 2015 and first published on 27 Jan 2015


Article type: Paper
DOI: 10.1039/C4OB02582B
Author version available: Download Author version (PDF)
Citation: Org. Biomol. Chem., 2015,13, 3331-3340
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    Synthesis of the tricyclic core of manzamine A

    R. B. Pathak, B. C. Dobson, N. Ghosh, K. A. Ageel, M. R. Alshawish, R. Saruengkhanphasit and I. Coldham, Org. Biomol. Chem., 2015, 13, 3331
    DOI: 10.1039/C4OB02582B

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