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Synthesis of higenamine, A cardiotonic principle of aconite root

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Abstract

Higenamine (I), a cardiotonic principle of Aconite root, was synthesized from 4-methoxy-phenylacetic acid (II) and β-(3, 4-dimethoxyphenyl)-ethylamine (IV). Condensation ofIV with 4-methoxyphenylacetyl chloride (III) was followed by cyclodehydration yielding 1-(4′-methoxybenzyl)-6,7-dimethoxy-3,4-dihydroisoquinoline (VI). Reduction ofVI to 1, 2, 3, 4-tetrahydroisoquinoline (VII) and subsequent demethylation provided desired product higenamine, 1-(4′-hydroxybenzyl)-6, 7-dihydroxy-1, 2, 3, 4-tetrahydroisoquinoline.

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  1. Ki-Churl Chang

    Present address: Department of Pharmacology, Medical College, Gyeong Sang National University, 620, Jinju, Korea

Authors and Affiliations

  1. College of Medicine, Seoul National University, 110, Seoul, Korea

    Ki-Churl Chang, Jung-Kyoo Lim & Chan-Woong Park

  2. Natural Products Research Institute, Seoul National University, 110, Seoul, Korea

    Hye Sook Yun-Choi

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  1. Ki-Churl Chang
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  2. Hye Sook Yun-Choi
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  3. Jung-Kyoo Lim
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Chang, KC., Yun-Choi, H.S., Lim, JK. et al. Synthesis of higenamine, A cardiotonic principle of aconite root. Arch. Pharm. Res. 7, 133–136 (1984). https://doi.org/10.1007/BF02856626

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  • DOI: https://doi.org/10.1007/BF02856626

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