Search Results:　 1-11 of 11

Hanaoka Miyoji , Kohzu Masumi , Yasuda Shingo

(±)-Raddeanone (1) was stereoselectively synthesized from the corresponding protoberberine (5) <via>___- the katal (17) in four steps.Inversion of a hydroxyl group in the katal (17) was realized …

Chemical & pharmaceutical bulletin 36(10), 4248-4251, 1988-10-25

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SENER Bilge

International Symposium on the Chemistry of Natural Products 1988, 189, 1988-05-29

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Hanaoka Miyoji , Kohzu Masumi , Yasuda Shingo

… A novel and stereoselective synthesis of (±)-sibiricine (1), a spirobenzylisoquinoline alkaloid, from the corresponding protoberberine (3) was developed using photo-oxygenation and photo-isomerization. …

Chemical & pharmaceutical bulletin 33(6), 2621-2623, 1985-06-25

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HANAOKA MIYOJI , INOUE MITSURU , TAKAHASHI MISAO , YASUDA SHINGO

… Berberine (14) was converted to the spirobenzylisoquinoline (18) through regioselective cleavage of the 8,14-cycloberbine (17). … Alkaline hydrolysis of the oxazolidinone (20) derived from 18 efficiently afforded the 11,12-oxygenated protoberberine (23), which was also obtained from 8-methoxyberberinephenolbetaine (24) through treatment of the keto-hydroxy-spirobenzylisoquinoline (25) with alkali. …

Chemical & pharmaceutical bulletin 32(11), 4431-4436, 1984-11-25

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Hanaoka M. , Mukai C. , Sakurai S. , Ashimori A. , Yamagishi H. , Iwasaki M. , Yasuda S.

… Stereoselective total syntheses of spirobenzylisoquinoline alkaloid (±)-ochrobirine and benzindenoazepine alkaloids fumarofine, O-methylfumarofine, and (±)-fumaritrine were accomplished from biogenetic precursors, protoberberines via 8,14-cycloberbines. … Synthesis of Spirobenzylisoquinoline Alkaloid (±)-Ochrobirine Stereoselective reduction of the cycloberbine (14) derived from coptisine (12) with LiAlH(OBu^t)_3, followed by treatment with ClCO_2Et gave the oxazolidinone (17). …

天然有機化合物討論会講演要旨集 (26), 414-421, 1983-09-15

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KATO AKIRA , AKAGI KIMIKO , IRIE HIROSHI , UYEO SHOJIRO

… The mass spectrometric fragmentation pattern of 21 kinds of fumariline alkaloids of the spirobenzylisoquinoline type was studied. …

Journal of the Pharmaceutical Society of Japan 95(9), 1058-1064, 1975-09-25

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