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

MIYOJI HANAOKA; MITSURU INOUE; NOBUYUKI KOBAYASHI; SHINGO YASUDA

doi:10.1248/cpb.35.980

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

MIYOJI HANAOKA, MITSURU INOUE, NOBUYUKI KOBAYASHI, SHINGO YASUDA

著者情報

キーワード: rhoeadine alkaloid, protoberberine alkaloid, cis-alpinigenine, cis-alpinine, palmatine, benzindenoazepine framework, 8, 14-cycloberbine, photooxygenation, photochemical isomerization, regioselective C-N bond cleavage

ジャーナルフリー

1987 年 35 巻 3 号 p. 980-985

DOI https://doi.org/10.1248/cpb.35.980

詳細

抄録

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.

責任著者(Corresponding author)

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