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Issue 11, 2016
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Total synthesis of Sceletium alkaloids (±)-joubertinamine, (±)-epijoubertinamine, (±)-tortuosamine and formal synthesis of (±)-mesembrine, (±)-N-formyltortuosamine

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Abstract

An efficient collective formal/total synthesis of Sceletium alkaloids and their seco-congeners has been reported. The bicyclic core of (±)-mesembrine, (±)-tortuosamine, and (±)-N-formyltortuosamine with all required functionalities including the characteristic quaternary benzylic carbon is achieved by employing the Wittig olefination–Claisen rearrangement protocol and synergistic Cu(I)/iminium catalyzed [3 + 3] condensation of O-acetylketoxime and α,β-unsaturated aldehyde (acrolein).

Graphical abstract: Total synthesis of Sceletium alkaloids (±)-joubertinamine, (±)-epijoubertinamine, (±)-tortuosamine and formal synthesis of (±)-mesembrine, (±)-N-formyltortuosamine

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Publication details

The article was received on 26 Feb 2016, accepted on 16 Sep 2016 and first published on 19 Sep 2016


Article type: Paper
DOI: 10.1039/C6NJ00630B
Citation: New J. Chem., 2016,40, 9432-9440
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    Total synthesis of Sceletium alkaloids (±)-joubertinamine, (±)-epijoubertinamine, (±)-tortuosamine and formal synthesis of (±)-mesembrine, (±)-N-formyltortuosamine

    V. A. Bhosale, D. U. Ukale and S. B. Waghmode, New J. Chem., 2016, 40, 9432
    DOI: 10.1039/C6NJ00630B

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