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A Total Synthesis of (±)-3-O-Demethylmacronine through Rearrangement of a Precursor Embodying the Haemanthidine Alkaloid Framework

Ma, Xiang; Gao, Yuqian (Nadia); Banwell, Martin; Carr, Paul D; Willis, Anthony


A total synthesis of the racemic modification, (±)-2, of the tazettine-type alkaloid 3-O-demethylmacronine is described. The key steps are an intramolecular Alder-ene (IMAE) reaction and a lactam-to-lactone rearrangement of tetracycle 13, a compound that embodies the haemanthidine alkaloid framework.

CollectionsANU Research Publications
Date published: 2017
Type: Journal article
Source: Journal of Organic Chemistry
DOI: 10.1021/acs.joc.7b00340
Access Rights: Open Access


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