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Cascade cyclization and intramolecular nitrone dipolar cycloaddition and formal synthesis of 19-hydroxyibogamine

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Abstract

A cascade or domino sequence of condensation of hydroxylamine and an aldehyde to give an oxime, cyclization to a nitrone, and intramolecular 1,3-dipolar cycloaddition has been successfully employed where there is branching at C-4 as a route to the iboga alkaloids. Cyclization occurs with displacement of chloride as a leaving group and intramolecular cycloaddition occurs with an alkene as a dipolarophile. The reaction gives an azabicyclo[2.2.2]octane product containing a fused isoxazolidine as a single stereoisomer and this was converted to an isoquinuclidine that completed a formal synthesis of the alkaloid (±)-19-hydroxyibogamine.

Graphical abstract: Cascade cyclization and intramolecular nitrone dipolar cycloaddition and formal synthesis of 19-hydroxyibogamine

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Publication details

The article was received on 14 Nov 2018, accepted on 05 Dec 2018 and first published on 05 Dec 2018


Article type: Paper
DOI: 10.1039/C8OB02839G
Citation: Org. Biomol. Chem., 2019, Advance Article
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    Cascade cyclization and intramolecular nitrone dipolar cycloaddition and formal synthesis of 19-hydroxyibogamine

    Z. T. I. Alkayar and I. Coldham, Org. Biomol. Chem., 2019, Advance Article , DOI: 10.1039/C8OB02839G

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