Open AccessA Total Synthesis of (±)-3-O-Demethylmacronine through Rearrangement of a Precursor Embodying the Haemanthidine Alkaloid Framework
Author(s) -
Xiang Ma,
Nadia Gao,
Martin G. Banwell,
Paul D. Carr,
Anthony C. Willis
Publication year - 2017
Publication title -
the journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.2
H-Index - 228
eISSN - 1520-6904
pISSN - 0022-3263
DOI - 10.1021/acs.joc.7b00340
Subject(s) - alkaloid , intramolecular force , total synthesis , lactam , stereochemistry , chemistry , lactone , cope rearrangement
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.
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