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Issue 14, 2018
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An expeditious route to the synthesis of the enantioenriched tetracyclic core of ergot alkaloids via an organocatalytic aldol reaction

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Abstract

The synthesis of the tetracyclic skeleton of ergot alkaloids has been developed via a key organocatalytic enantioselective aldol reaction using paraformaldehyde as the C1-unit in the presence of thiourea catalyst followed by a key Pd-catalyzed directed coupling accelerated by the DavePhos ligand. Utilizing the aforementioned strategy, we have synthesized a key tetracyclic intermediate in up to 95% ee with high yield.

Graphical abstract: An expeditious route to the synthesis of the enantioenriched tetracyclic core of ergot alkaloids via an organocatalytic aldol reaction

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Publication details

The article was received on 11 Dec 2017, accepted on 07 Mar 2018 and first published on 08 Mar 2018


Article type: Paper
DOI: 10.1039/C7OB03069J
Citation: Org. Biomol. Chem., 2018,16, 2427-2437
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    An expeditious route to the synthesis of the enantioenriched tetracyclic core of ergot alkaloids via an organocatalytic aldol reaction

    S. Bhunia, S. Chaudhuri, S. De, K. N. Babu and A. Bisai, Org. Biomol. Chem., 2018, 16, 2427
    DOI: 10.1039/C7OB03069J

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