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Chin. J. Org. Chem. ›› 1992, Vol. 12 ›› Issue (1): 87-91. Previous Articles Next Articles
Original Articles
邓定安;蔡俊超
发布日期:
DENG DINGAN;CAI JUNCHAO
Published:
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The title compounds I are useful intermediates in the synthesis of tetrahydroisoquinoline alkaloids. (RS)-1-(3-Bromo-4-methoxy)benzyl-6-methoxy-7-benzyloxy-3,4-dihydroi soquinoline was reduced to (RS)-1-(3-bromo-4-methoxy)benzyl-6-methoxy-7-benzyloxy-1,2,3,4-tetr ahydroisoquinoline (II) by NaBH4. II was resolved with di-p-toluoyl-D-(-)-tartaric acid and the enantiomers were converted to the N-Me derivatives with CH2O and HCO2H resp., followed by hydrolysis with HCl to give I. Abs. configurations of I were assigned based on sp. rotation and ORD curves by using the convention and sequence rule (+) = S = (L); (-) = R = (D) in the benzyltetrahydroisoquinoline series.
Key words: MESOTOMY, PROTON MAGNETIC RESONANCE SPECTROMETRY, QUINOLINE P, STEREOISOMERISM
CLC Number:
O621
DENG DINGAN;CAI JUNCHAO. Synthesis of R and S-1-(3'-bromo-4'-methoxy) benzyl-2-methyl-6-methoxy-7-hydroxy-1,2,3,4-tetrahydroisoquinoline[J]. Chin. J. Org. Chem., 1992, 12(1): 87-91.
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