Art

J-GLOBAL ID：200902232582760276   Reference number：03A0849948

A Synthesis of Chiral 1,1,3-Trisubstituted 1,2,3,4-Tetrahydro-β-carbolines by the Pictet-Spengler Reaction of Tryptophan and Ketones: Conversion of (1R,3S)-Diastereomers into Their (1S,3S)-Counterparts by Scission of the C(1)-N(2) Bond

トリプトファンとケトン類とのPictet-Spengler反応によるキラル1,1,3-三置換1,2,3,4-テトラヒドロ-β-カルボリン類の合成: C(1)-N(2)結合の切断による(1R,3S)-ジアステレオマの(1S,3S)-対応物ヘの変換

Author (4)： HORIGUCHI Y (Showa Pharmaceutical Univ., Tokyo, JPN) ,  NAKAMURA M (Showa Pharmaceutical Univ., Tokyo, JPN) ,  SAITOH T (Showa Pharmaceutical Univ., Tokyo, JPN) ,  SANO T (Showa Pharmaceutical Univ., Tokyo, JPN)
Material： Chemical and Pharmaceutical Bulletin  (Chemical & Pharmaceutical Bulletin)
Volume： 51  Issue： 12  Page： 1368-1373  Publication year： Dec. 01, 2003 
JST Material Number： G0504A  ISSN： 0009-2363  CODEN： CPBTAL  Document type： Article
Article type： 原著論文  Country of issue： Japan (JPN)  Language： ENGLISH (EN)

Thesaurus term： *nitrogen heterocyclic compound ,...
Semi thesaurus term： kinematic control ,...

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JST classification (2)： Other condensed derivatives of pyridine  (CF07097Y) ,  Cyclization reaction,ring-opening reaction  (CF02050I)

Substance index (19)： L-Tryptophan methyl ,  Acetophenone ,  4'-Chloroacetophenone ,  4'-Methoxyacetophenone ,  Titanium(IV)tetraisopropoxide ,  N^α-(1-Phenylethylidene)-L-tryptophan isopropyl ester ,  N^α-[1-(4-Chlorophenyl)ethylidene]-L-tryptophan isopropyl ester ,  N^α-[1-(4-Methoxyphenyl)ethylidene]-L-tryptophan isopropyl ester ,  (1S)-1α-Phenyl-1-methyl-1,2,3,4-tetrahydro-β-carboline-3α-carboxylic acid isopropyl ester ,  (1S)-1α-(4-Chlorophenyl)-1-methyl-1,2,3,4-tetrahydro-β-carboline-3α-carboxylic acid isopropyl ester ,  (1S)-1α-(4-Methoxyphenyl)-1-methyl-1,2,3,4-tetrahydro-β-carboline-3α-carboxylic acid isopropyl ester ,  (1R)-1α-Methyl-1-phenyl-1,2,3,4-tetrahydro-β-carboline-3α-carboxylic acid isopropyl ester ,  (1R)-1α-Methyl-1-(4-chlorophenyl)-1,2,3,4-tetrahydro-β-carboline-3α-carboxylic acid isopropyl ester ,  (1R)-1α-Methyl-1-(4-methoxyphenyl)-1,2,3,4-tetrahydro-β-carboline-3α-carboxylic acid isopropyl ester ,  D-Tryptophan methyl ,  (1R)-1α-Methyl-1-phenyl-1,2,3,4-tetrahydro-β-carboline-3β-carboxylic acid isopropyl ester ,  (1S)-1α-Phenyl-1-methyl-1,2,3,4-tetrahydro-β-carboline-3β-carboxylic acid isopropyl ester ,  (R)-2-Phenyl-2-methoxy-3,3,3-trifluoropropionic acid [(1R)-1α-methyl-1-phenyl-1,2,3,4-tetrahydro-β-carboline-3α-yl]methyl ester ,  (R)-2-Phenyl-2-methoxy-3,3,3-trifluoropropionic acid [(1S)-1α-phenyl-1-methyl-1,2,3,4-tetrahydro-β-carboline-3β-yl]methyl ester

Reference (14)：

• 1) Pictet A., Spengler T., Chem. Ber., 44, 2030 (1911).
• 2) Bringmann G., Ewers C. T., Walter R., “Comprehensive Organic Synthesis,” Vol. 6, ed. by Trost B. M., Fleming I., Pergamon Press, Oxford, 1991, pp. 736—740.
• 3) Recent Review: Cox E. D., Cook J. M., Chem. Rev., 95, 1797—1842 (1995).
• 4) Horiguchi Y., Kodama H., Nakamura M., Yoshimura T., Hanezi K., Hamada H., Saitoh T., Sano T., Chem. Pharm. Bull., 50, 253—257 (2002).
• 5) Horiguchi Y., Nakamura M., Kida A., Kodama H., Saitoh T., Sano T., Heterocycles, 59, 691—705 (2003).

Terms in the title (7)： トリプトファン ,  ケトン類 ,  Pictet-Spengler反応 ,  キラル ,  置換 ,  β-カルボリン ,  ジアステレオマ