Concise stereocontrolled formal synthesis of (±)-quinine and total synthesis of (±)-7-hydroxyquinine via merged Morita-Baylis-Hillman-Tsuji- Trost cyclization

Journal of Organic Chemistry

Volumn 73, Issue 23, 2008, Pages 9379-9387

  Webber, Peter ^a   Krische, Michael J ^a  

^a UNIVERSITY OF TEXAS AT AUSTIN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETONE; AMINES; CHEMICAL REACTIONS; CYCLIZATION; KETONES; OLEFINS; ORGANIC COMPOUNDS; RATE CONSTANTS; STEREOCHEMISTRY; STEREOSELECTIVITY; VANADIUM COMPOUNDS;

ALLYL CARBONATES; ALLYLIC ACETATES; ALLYLIC ALCOHOLS; AMINOACETALDEHYDE; ASYMMETRIC INDUCTIONS; CARBON ATOMS; CARBONYL REDUCTIONS; CHEMICAL EQUATIONS; DEOXYGENATION; DIASTEREOSELECTIVE; FORMAL SYNTHESES; METHYL KETONES; OXOVANADIUM; PROTECTING GROUPS; STEREOCENTERS; STEREOSELECTIVE; STEREOSELECTIVE FORMATIONS; STEREOSELECTIVE SYNTHESIS; TOTAL SYNTHESES;

SYNTHESIS (CHEMICAL);

1 [1(2,4,6 TRIISOPROPYL BENZENESULFONYL) 3 VINYL 1,2,3,6 TETRAHYDRO PYRIDIN 4 YL]ETHANONE; 1 [1(TOLUENE 4 SULFONYL) 3 VINYL 1,2,3,6 TETRAHYDRO PYRIDIN 4 YL]ETHANONE; 4 ACETYL 3 VINYL PIPERIDINE 1 CARBOXVLIC ACID TERT BUTYL ESTER; 4 ACETYL 3 VINYL PIPERIDINE 1 CARBOXYLIC ACID BENZYL ESTER; 4 [1 ACETOXY 3 (6 METHOXY QUINOLIN 4 YL)ALLYL] 3 VINYL PIPERIDINE 1 CARBOXYLIC ACID BENZYL ESTER; 4 [1 HYDROXY 3 (6 METHOXY QUINOLIN 4 YL)ALLYL] 3 VINYL PIPERIDINE 1 CARBOXYLIC ACID BENZYL ESTER; 4 [1 HYDROXY 3(6 METHOXY QUINOLIN 4 YL)ALLYL] 3 VINYL PIPERIDINE 1 CARHOXYLIC ACID TERT BUTYL ESTER; 4 [3 (6 METHOXY QUINOLIN 4 YL)ACRYLOYL] 3 VINYL PIPERIDINE 1 CARHOXYLIC ACID TERT BUTYL ESTER; 4 [3 (6 METHOXY QUINOLIN 4 YL)ACRYLOYL]4 ACETYL 3 VINYL PIPERIDINE 1 CARBOXYLIC ACID BENZYL ESTER; 4 [3 (6 METHOXY QUINOLIN 4 YL)ALLYL] 3 VINYL PIPERIDINE 1 CARBOXYLIC ACID BENZYL ESTER; 4 [HYDROXY [3 (6 METHOXY QUINOLIN 4 YL)OXIRANYL]METHYL] 3 VINYL PIPERIDINE 1 CARHOXYLIC ACID TERT BUTYL ESTER; 7 HYDROXY 9 (4 METHOXYBENZYLOXY)QUININE; 7 HYDROXY 9 (METHOXYBENZYLOXY)QUININE; 7 HYDROXYQUININE; ACETIC ACID; ACETONE; ALKENE; ALLYL ALCOHOL; CARBONIC ACID; ELECTROPHILE; OXOVANADIUM; QUININE DERIVATIVE; UNCLASSIFIED DRUG; VANADIUM DERIVATIVE; 7-HYDROXYQUINOLINE; AMINE; CARBON; QUINOLINOL DERIVATIVE; QUINONE DERIVATIVE; SOLVENT;

ALDOL REACTION; ALLYLATION; ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; CYCLIZATION; DEOXYGENATION; DRUG SYNTHESIS; EPOXIDATION; MORITA BAYLIS HILLMAN TSUJI TROST REACTION; STEREOCHEMISTRY; CHEMICAL MODEL; CHEMISTRY; ORGANIC CHEMISTRY; PROCEDURES; STEREOISOMERISM; SYNTHESIS;

AMINES; CARBON; CATALYSIS; CHEMISTRY, ORGANIC; HYDROXYQUINOLINES; MODELS, CHEMICAL; QUINONES; SOLVENTS; STEREOISOMERISM;

EID: 57449114517     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo802165k     Document Type: Article

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