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Asymmetric formal synthesis of (+)-cycloclavine

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Abstract

The asymmetric synthesis of Szántay's amine (+)-2, the pivotal precursor for direct access to (+)-cycloclavine (1), is described for the first time in eleven steps with 19.7% overall yield from the commercially available 4-bromoindole. The strategy features an asymmetric induction by Ellman's sulfinimine and rhodium-catalysed isomerization of the C[double bond, length as m-dash]C bond.

Graphical abstract: Asymmetric formal synthesis of (+)-cycloclavine

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Publication details

The article was received on 18 Oct 2017, accepted on 30 Oct 2017 and first published on 30 Oct 2017


Article type: Communication
DOI: 10.1039/C7CC08044A
Citation: Chem. Commun., 2017, Advance Article
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    Asymmetric formal synthesis of (+)-cycloclavine

    J. Chen, L. Song, F. Li, Z. Shi and X. Cao, Chem. Commun., 2017, Advance Article , DOI: 10.1039/C7CC08044A

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