First total syntheses of aeruginosin 298-A and aeruginosin 298-B, based on a stereocontrolled route to the new amino acid 6-hydroxyoctahydroindole-2-carboxylic acid

Chemistry - A European Journal

Volumn 7, Issue 16, 2001, Pages 3446-3460

  Valls, Nativitat ^a   López Canet, Meritxell ^a   Vallribera, Mercè ^a   Bonjoch, Josep ^a  

^a UNIVERSITY OF BARCELONA   (Spain)

Author keywords

Aeruginosins; Amino acids; Peptides; Thrombin inhibitor; Total synthesis

Indexed keywords

AMINO ACIDS; CARBOXYLIC ACIDS; HYDROGENATION; ISOMERS; STEREOCHEMISTRY;

PUTATIVE STRUCTURES;

SYNTHESIS (CHEMICAL);

4 HYDROXYPHENYLLACTIC ACID; 6 HYDROXYOCTAHYDROINDOLE 2 CARBOXYLIC ACID; AERUGINOSIN 298 A; AERUGINOSIN 298 B; ALCOHOL; ALPHA AMINO ACID; AMINO ACID DERIVATIVE; ANISOLE DERIVATIVE; ARGININE; CARBOXYLIC ACID DERIVATIVE; DIHYDROANISOLE; LACTIC ACID DERIVATIVE; LEUCINE; TYROSINE; UNCLASSIFIED DRUG;

ACIDITY; ARTICLE; CHEMICAL STRUCTURE; CYCLIZATION; HYDROGENATION; REDUCTION; SPECTROSCOPY; STEREOCHEMISTRY; STEREOISOMERISM; SYNTHESIS;

ANTITHROMBINS; INDICATORS AND REAGENTS; INDOLES; LEUCINE; MODELS, MOLECULAR; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 0035902879     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/1521-3765(20010817)7:16<3446::AID-CHEM3446>3.0.CO;2-0     Document Type: Article

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65. For analytical data see Supporting Information.
66. The optical rotation value corresponds to that of a sample obtained from the recrystallyzed Hpla derivative 34 (ee >98%).