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페놀베타인 유도체합성: 프로토베르베린에서 C-환의 관능기도입 및 BC-환의 화학적 변환

Synthesis of Phenolbetaine Derivatives Introduction of Functional Groups to C-ring and Chemical Transformation of BC-ring of Protoberberine

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Betaine was treated with hydrochloric acid and then with sodium borohydride to give a hydroxy compound 2. The reaction of 2 with thionyl chloride followed by thiourea led a compound 5. Oxidation of compound 2 with pyridinium dichromate(PDC) and succesive treatment with Lawesson''s reagent also afforded the same compound 5. Cleavage of N-C14 bond compound of 7 was carried out via two reaction sequence from the compound 4. Finally, compound 10 was sythesized by a series of transformations from the compound 4.

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