Stereoselective synthesis of constrained oxacyclic hydroxyethylene isosteres of aspartic protease inhibitors: Aldol and Mukaiyama aldol methodologies for branched tetrahydrofuran 2-carboxylic acids

Journal of Organic Chemistry

Volumn 70, Issue 17, 2005, Pages 6735-6745

  Hanessian, Stephen ^a   Hou, Yihua ^a   Bayrakdarian, Malken ^a   Tintelnot Blomley, Marina ^b  

^a UNIVERSITÉ DE MONTRÉAL   (Canada)

^b NOVARTIS PHARMA AG   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDES; CATALYSIS; CONDENSATION; DISEASES; ETHERS; ISOMERS; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

ALDOL; ENOL SILYL ETHERS; ENOLATES; STEREOSELECTIVE SYNTHESIS;

CARBOXYLIC ACIDS;

3 (1 HYDROXYL 2 TERT BUTOXYCARBONYLAMINO)TETRAHYDROFURAN 2 CARBOXYLIC ACID BUTYLAMIDE; 3 (2 DIBENZYLAMINO 1 HYDROXY 3 PHENYLPROPYL)DIHYDROFURAN 2 ONE; 3 (2 DIBENZYLAMINO 1 HYDROXY 4 METHYLPENTYL)DIHYDROFURAN 2 ONE; 3 (2 DIBENZYLAMINO 1 HYDROXYPROPYL)DIHYDROFURAN 2 ONE; 3 (2 TERT BUTOXYCARBONYLAMINO 1 HYDROXY 4 METHYLPENTYL)DIHYDROFURAN 2 ONE; 3 [(1 TERT BUTYLDIMETHYLSILANYLOXY) 2 DIBENZYLAMINO 4 METHYLPENTYL]TETRAHYDROFURAN 2 CARBALDEHYDE; 3 [(1 TERT BUTYLDIMETHYLSILANYLOXY) 2 DIBENZYLAMINO 4 METHYLPENTYL]TETRAHYDROFURAN 2 CARBOXYLIC ACID; 3 [(1 TERT BUTYLDIMETHYLSILANYLOXY) 2 DIBENZYLAMINO 4 METHYLPENTYL]TETRAHYDROFURAN 2 CARBOXYLIC ACID BUTYLAMIDE; 3 [(1 TERT BUTYLDIMETHYLSILANYLOXY) 2 DIBENZYLAMINO 4 METHYLPENTYL]TETRAHYDROFURAN 2 CARBOXYLIC ACID METHYL ESTER; 3 [(1 TERT BUTYLDIMETHYLSILANYLOXY) 2 DIBENZYLAMINO 4 METHYLPENTYL]TETRAHYDROFURAN 2 CARBOXYLIC ACID N BUTYLVALINAMIDE; 3 [(1 TERT BUTYLDIMETHYLSILANYLOXY) 2 DIBENZYLAMINO 4 METHYLPENTYL]TETRAHYDROFURAN 2 CARBOXYLIC ACID N METHYLALANINAMIDE; 3 [1 (TERT BUTYLDIMETHYLSILANYLOXY 2 DIBENZYLAMINO 4 METHYLPENTYL)]DIHYDROFURAN 2 ONE; 4 HYDROXY (2 HYDROXYETHYL) 5 ISOBUTYLPYRROLIDIN 2 ONE; AMINOALCOHOL; GAMMA BUTYROLACTONE; OM 99 2; PROTEINASE INHIBITOR; TETRAHYDROFURAN DERIVATIVE; UNCLASSIFIED DRUG; YTTERBIUM;

ALDOL REACTION; ALZHEIMER DISEASE; ARTICLE; CATALYSIS; DIASTEREOISOMER; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME INHIBITION; MUKAIYAMA REACTION; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION;

ALDEHYDES; ASPARTIC ENDOPEPTIDASES; CARBOXYLIC ACIDS; ETHYLENES; FURANS; MAGNETIC RESONANCE SPECTROSCOPY; MASS SPECTROMETRY; PROTEASE INHIBITORS; SPECTROPHOTOMETRY, INFRARED;

EID: 23644459258     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo050749y     Document Type: Article

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