Neoxyberberine—acetone

Berberinephenolbetaine (121) was first obtained by Pyman and designated as neoxyberberine (79). Acetoneberberine (119) was oxidized with potassium permanganate in aqueous acetone to give neoxyberberine acetone (120), the structure of which was established by Iwasa and Naruto (80). On treatment with hydrochloric acid followed by sodium hydroxide, 120 gave 121 (79-81), which was also obtained directly from 119 by oxidation with potassium permanganate or osmium tetroxide (Scheme 26) (80). 

Berberine-acetone when subjected to mild permanganate oxidation is converted to neoxyberberine-acetone and to the lactamic acid 43 reminiscent of Perkin s berberal. ... 

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