Issue 1, 2019

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

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

Supplementary files

Article information

Article type
Paper
Submitted
14 Nov 2018
Accepted
05 Dec 2018
First published
05 Dec 2018

Org. Biomol. Chem., 2019,17, 66-73

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

Z. T. I. Alkayar and I. Coldham, Org. Biomol. Chem., 2019, 17, 66 DOI: 10.1039/C8OB02839G

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