A Total Synthesis of (±)-3-O-Demethylmacronine through Rearrangement of a Precursor Embodying the Haemanthidine Alkaloid Framework
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Ma, Xiang; Gao, Yuqian (Nadia); Banwell, Martin
; Carr, Paul D; Willis, Anthony
Description
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.
| Collections | ANU Research Publications |
|---|---|
| Date published: | 2017 |
| Type: | Journal article |
| URI: | http://hdl.handle.net/1885/219195 |
| Source: | Journal of Organic Chemistry |
| DOI: | 10.1021/acs.joc.7b00340 |
| Access Rights: | Open Access |
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| File | Description | Size | Format | Image |
|---|---|---|---|---|
| Total Synthesis of (±)-3-O-Demethylmacronine R1.pdf | 332.46 kB | Adobe PDF |  |
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