New reactivities of deltaline analogs: an efficient O-demethylation at C-1 and an unusual extrusion of the C-14 atom
作者： Pei Tang , Qi-Feng Chen , Ling Wang , Qiao-Hong Chen , Xi-Xian Jian
DOI: 10.1016/J.TET.2012.04.055
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摘要: Abstract O-Demethylation at C-1 in the C19-diterpenoid alkaloids is very challenging. In this paper, it was firstly observed that 10-OH group deltaline (1) a determining factor for O-demethylation reaction. After removal of hydroxyl group, 1-O-methyl corresponding analogs can be readily removed by treatment with HBr–HOAc. Meanwhile, C-14 atom bromides 18 or 20 extruded under basic condition probably via sequence, including Grob fragmentation, aerobic oxidation, deformylation, and SN2 nucleophilic substitution, to give enone 21 (70%) oxetane 22 (14%). The structure compound confirmed X-ray crystallographic analysis its derivative 21.
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