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Chemical Transformation of Protoberberines. XII. : A Novel Synthesis of Rhoeadine Alkaloids. : An Alternative Synthesis of a Key Intermediate, Benzindenoazepine, for a Synthesis of (±)-cis-Alpinigenine and (±)-cis-Alpinine from Palmatine(Organic,Chemical)
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HANAOKA MIYOJI
,
INOUE MITSURU
,
KOBAYASHI NOBUYUKI
,
YASUDA SHINGO
… A formal synthesis of (±)-cis-alpinigenine (3) and (±)-cis-alpinine (4) was achieved by conversion of palmatine (7) into the key intermediate, benzindenoazepine (16), via the ring D-inverted 2,3,11,12-tetraoxygenated phenolbetaine (14) and the 8,14-cycloberbine (15) through photooxygenation, photochemical valence isomerization, and regioselective C-N bond cleavage of 15 as crucial reactions. …
Chemical & pharmaceutical bulletin 35(3), 980-985, 1987-03-25
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