Studies on the Alkaloids of Papaveraceous Plants. XXX. Conformational Analysis of Some Hydrobenzo [c]-phenanthridine-type Alkaloids

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In some hydrobenzo [c] phenanthridine-type alkaloids, the preferred conformation of the B and C rings in solution and the orientation of the N-methyl group in solution and in crystalline state were examined using infrared, proton magnetic resonance, and carbon magnetic resonance spectroscopies. The alkaloids, chelidonine (1), corynoline (2), 6-quasi-axial and quasi-equatorial alkyl-substituted derivatives of 2 (2a'-c' and 2a-c), and corynolamine (3), exist in the conformation with type I-cis and B/C-half chair/half chair, 6-quasi-axial alkyl-substituted derivatives of 2-acetate (2b'-Ac and 2a'-Ac) and 3-diacetate adopt the conformation with type I-cis and B/C-twist half-chair/half chair, and 2-acetate and its 6-quasi-equatorial alkylsubstituted derivatives (2a-Ac and 2b-Ac) possess the conformation with type I-cis and B/C-half chair/twist halfboat. Chelidonine acetate (1-Ac) exists in the conformation with type II-cis and B/C-half chair/twist half-chair. (+)-14-Epicorynoline (4) and its acetate adopt the conformation with trans and B/C-half chair-twist half-chair. The preferred conformation of the N-methyl group in solution in 1,2,2a-c, 2a'-c', 2a-Ac, 2b-Ac, and 3 is equatorial and that in 1-acetate, 2a'-Ac, 2b'-Ac, 3-diacetate, 4,and 4-acetate is axial. In 2-acetate, the position of equilibrium in the N-Me(ax)⇄N-Me-(eq) shifts to the equatorial side than the axial side. Orientation of the N-methyl group in a crystalline state is in accord with the preferred conformation in solution.
公益社団法人日本薬学会の論文
1978-06-25

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