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

Ma, XiangGao, Yuqian (Nadia)Banwell, MartinCarr, Paul DWillis, Anthony2021-01-062021-01-060022-3263http://hdl.handle.net/1885/219195A 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.We thank the Australian Research Council for financial support. X.M. is the grateful recipient of a PhD Scholarship provided by the Guangzhou Elite Project of the Guangzhou Municipal Government, People’ s Republic of China.application/pdfen-AU© 2017 American Chemical SocietyA Total Synthesis of (±)-3-O-Demethylmacronine through Rearrangement of a Precursor Embodying the Haemanthidine Alkaloid Framework201710.1021/acs.joc.7b003402020-11-23