| Co-Investigator(Kenkyū-buntansha) |
YOSHIDA Shuji Faculty of Pharmaceutical Sciences,Kanazawa University, 薬学部, 教務職員 (10191587)
MUKAI Chisato Faculty of Pharmaceutical Sciences,Kanazawa University, 薬学部, 助手 (70143914)
YASUDA Shingo Faculty of Pharmaceutical Sciences,Kanazawa University, 薬学部, 助教授 (00019663)
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| Budget Amount *help |
¥6,000,000 (Direct Cost: ¥6,000,000)
Fiscal Year 1987: ¥1,200,000 (Direct Cost: ¥1,200,000)
Fiscal Year 1986: ¥4,800,000 (Direct Cost: ¥4,800,000)
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| Research Abstract |
1,Regioselective synthesis of 2,3,9,10-oxygenated protoberbering alkaloids was developed starting from readily available benzaldehydes and phenethyl amines.
2.2,3,9,10-oxygenated protoberbering were converted to2,3,10,11-oxygenated protoberberines through C_8-C_<8a> bond cleavage followed by photo-cyclization.
3.Biomimetic and efficient conversion of berbering to chelerythrine was achieved through regioselective C_6-N bond cleavage,acetalization with thallium trinitrate, and then acidic cyclization.Fagaridine was synthesized from berberine via oxychelerythrine through selective demethylation.
4.The above synthetic method was applied to a convevient synthesis of antitumor alkaloids,nitidine and fagaronine.
5.This synthetic method was further confirmed tobe a general method for a synthesis of fully aromatized benzophenanthridine alkaloids by a synthesis of oxyterihanine and sanguilutine.
6.Chelidonine and chelamine were stereoselectively synthesized from coptisine through cationic cyclization,that established the stereochemistry of chelamine. Similarly,berbering was converted to homochelidonine and chelamidine.
7.The present synthesis provides a novel synthesis of both B/C-hexahybro-and fully aromatized benzophenanthridine alkaloids via common intermediates,which gave also sanguinarine and chelerythrine.
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