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The total synthesis of (±)-scoulerine was accomplished by Mannich reaction of 1-(2-bromo-5-hydroxy-4-methoxy-benzyl)-1,2,3,4-tetrahydro-7-hydroxy-6-methoxyisoquinoline, followed by debromination. Methylation of 12-bromoscoulerine and debromination of 12-bromotetrahydropalmatine afforded (±)-tetrahydropalmatine.
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Kametani et al. (1967) studied this question.
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