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

Chemical and Pharmaceutical Bulletin

Volumn 51, Issue 12, 2003, Pages 1368-1373

  Horiguchi, Yoshie ^a   Nakamura, Masayoshi ^a   Saitoh, Toshiaki ^a   Sano, Takehiro ^a  

^a SHOWA PHARMACEUTICAL UNIVERSITY   (Japan)

Author keywords

Aryl methyl ketone; Pictet spengler reaction; Stereoselectivity; Tetrahydro carboline; Tryptophan

Indexed keywords

BETA CARBOLINE DERIVATIVE; FORMIC ACID; IMINE; KETONE; REAGENT; TITANIUM; TRIFLUOROACETIC ACID; TRYPTOPHAN; CARBOLINE DERIVATIVE; DRUG DERIVATIVE;

ACIDITY; ARTICLE; CHEMICAL BOND; CHEMICAL REACTION KINETICS; CHIRALITY; CYCLIZATION; DIASTEREOISOMER; DRUG STABILITY; DRUG STRUCTURE; DRUG SYNTHESIS; PICTET SPENGLER REACTION; POLYMERIZATION; QUANTITATIVE ANALYSIS; STEREOCHEMISTRY; SUBSTITUTION REACTION; THERMODYNAMICS; STEREOISOMERISM; SYNTHESIS;

CARBOLINES; KETONES; STEREOISOMERISM; TRYPTOPHAN;

EID: 3142670809     PISSN: 00092363     EISSN: 13475223     Source Type: Journal    
DOI: 10.1248/cpb.51.1368     Document Type: Article

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