A Chiral Synthesis of Four Stereoisomers of 1,3-Dimethyl-1,2,3,4-tetrahydroisoquinoline, an Inducer of Parkinson-like Syndrome
スポンサーリンク
概要
- 論文の詳細を見る
Four stereoisomers of 1,3-dimethyl-1,2,3,4-tetrahydroisoquinoline, an inducer of Parkinson-like syndrome, were synthesized by applying a new method of 1,2,3,4-tetrahydroisoquinoline (TIQ) synthesis utilizing the Pummerer reaction as a key step. The chiral centers at C-1 and C-3 were constructed by two routes starting from alaninol (3) and 1-phenylethylamine (4) as a chiral source. Enantiomerically pure 1,3-dimethyl-TIQs (1R, 3S)-(1), (1S, 3R)-(ent-1), (1S, 3S)-(2), and (1R, 3R)-(ent-2) were prepared in a stereochemically unambiguous manner from 3 in 11 steps (route I) and from 4 in 6 steps (route II). The conformations of tetrahydroisoquinoline ring in 1-methyl, 3-methyl, and 1,3-dimethyl-TIQs were discussed on the basis of their CD, ^1H-NMR spectra, and steric energies.
- 公益社団法人日本薬学会の論文
- 2000-01-01
著者
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佐野 武弘
昭和薬科大学
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佐野 武弘
Showa Pharmaceutical Univ. Tokyo Jpn
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SANO Takehiro
Showa College of Pharmaceutical Sciences
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SAITOH Toshiaki
Showa College of Pharmaceutical Sciences
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TODA Jun
Showa College of Pharmaceutical Sciences
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Toda J
Showa Coll. Pharmaceutical Sci. Tokyo Jpn
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MATSUMOTO Shinobu
Showa College of Pharmaceutical Sciences
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