Modular synthesis of lamellarins via regioselective assembly of 3,4,5-differentially arylated pyrrole-2-carboxylates

Journal of Organic Chemistry

Volumn 79, Issue 2, 2014, Pages 529-537

  Komatsubara, Masashi ^a   Umeki, Teppei ^a   Fukuda, Tsutomu ^a   Iwao, Masatomo ^a  

^a NAGASAKI UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOXYLATION; SYNTHESIS (CHEMICAL);

AROMATIC RINGS; ARYLBORONIC ACIDS; DIMETHYL ACETAL; KEY REACTIONS; MODULAR SYNTHESIS; PALLADIUM-CATALYZED; REGIO-SELECTIVE; SUZUKI-MIYAURA COUPLING;

AROMATIC COMPOUNDS;

3 (2,2 DIMETHOXYETHYL) 7 ISOPROPOXY 1 (3 ISOPROPOXY 4 METHOXYPHENYL) 2 (4 ISOPROPOXY 3 METHOXYPHENYL) 8 METHOXY[1]BENZOPYRANO[3,4 B]PYRROL 4(3H) ONE; 3,11 DIHYDROXY 14 (3 HYDROXY 4 METHOXYPHENYL) 2,12 DIMETHOXY 6H [1]BENZOPYRANO [4',3':4,5]PYRROLO[2,1 A] ISOQUINOLIN 6 ONE; 3,11 DIHYDROXY 14 (3 HYDROXY 4 METHOXYPHENYL) 2,12 DIMETHOXY 8,9 DIHYDRO 6H [1]BENZOPYRANO [4',3':4,5]PYRROLO [2,1 A]ISOQUINOLIN 6 ONE; 3,11 DIISOPROPOXY 14 (3 ISOPROPOXY 4 METHOXYPHENYL) 2,12 DIMETHOXY 6H [1]BENZOPYRANO[4',3':4,5]PYRROLO[2,1 A] ISOQUINOLIN 6 ONE; 3,11 DIISOPROPOXY 14 (3 ISOPROPOXY 4 METHOXYPHENYL) 2,12 DIMETHOXY 8,9 DIHYDRO 6H [1]BENZOPYRANO[4',3':4,5] PYRROLO[2,1 A]ISOQUINOLIN 6 ONE; 3,11 DIISOPROPOXY 14 (3 ISOPROPOXY 4 METHOXYPHENYL) 2,12 DIMETHOXY 9 (PHENYLSULFANYL) 8,9 DIHYDRO 6H [1] BENZOPYRANO[4',3':4,5]PYRROLO[2,1 A]ISOQUINOLIN 6 ONE; 7 ISOPROPOXY 1 (3 ISOPROPOXY 4 METHOXYPHENYL) 2 (4 ISOPROPOXY 3 METHOXYPHENYL) 8 METHOXY 3 [2 (PHENYLSULFANYL) ETHYL][1]BENZOPYRANO[3,4 B]PYRROL 4(3H) ONE; 7 ISOPROPOXY 1 (3 ISOPROPOXY 4 METHOXYPHENYL) 2 (4 ISOPROPOXY 3 METHOXYPHENYL) 8 METHOXY 3 [2 (PHENYLSULFINYL) ETHYL][1]BENZOPYRANO[3,4 B]PYRROL 4(3H) ONE; 7 ISOPROPOXY 1 (3 ISOPROPOXY 4 METHOXYPHENYL) 2 (4 ISOPROPOXY 3 METHOXYPHENYL) 8 METHOXY[1]BENZOPYRANOL[3,4 B]PYRROL 4(3H) ONE; ALKALOID DERIVATIVE; BROMIDE; CARBOXYLIC ACID DERIVATIVE; LAMELLARIN; METHYL 3 (3,4 DIMETHOXYPHENYL) 4 (3 ISOPROPOXY 4 METHOXYPHENYL) 5 (4 ISOPROPOXY 3 METHOXYPHENYL) 1H PYRROLE 2 CARBOXYLATE; METHYL 3 (4,5 DIMETHOXY 2 METHOXYMETHOXYPHENYL) 4 (3 ISOPROPOXY 4 METHOXYPHENYL) 5 (4 ISOPROPOXY 3 METHOXYPHENYL) 1H PYRROLE 2 CARBOXYLATE; METHYL 3 BROMO 4 (3 ISOPROPOXY 4 METHOXYPHENYL) 5 (4 ISOPROPOXY 3 METHOXYPHENYL) 1H PYRROLE 2 CARBOXYLATE; METHYL 4 (3 ISOPROPOXY 4 METHOXYPHENYL) 5 (4 ISOPROPOXY 3 METHOXYPHENYL) 1H PYRROLE 2 CARBOXYLATE; METHYL 4 (3 ISOPROPOXY 4 METHOXYPHENYL) 5 (4 ISOPROPOXY 3 METHOXYPHENYL) 3 (3,4,5 TRIMETHOXYPHENYL) 1H PYRROLE 2 CARBOXYLATE; METHYL 4 (3 ISOPROPOXY 4 METHOXYPHENYL) 5 (4 ISOPROPOXY 3 METHOXYPHENYL) 3 (4 ISOPROPOXY 5 METHOXY 2 METHOXYMETHOXYPHENYL) 1H PYRROLE 2 CARBOXYLATE; METHYL 4 (3 ISOPROPOXY 4 METHOXYPHENYL) 5 (4 ISOPROPOXY 3 METHOXYPHENYL) 3 (4 METHOXYPHENYL) 1H PYRROLE 2 CARBOXYLATE; METHYL 4 (3 ISOPROPOXY 4 METHOXYPHENYL) 5 (4 ISOPROPOXY 3 METHOXYPHENYL) 3 PHENYL 1H PYRROLE 2 CARBOXYLATE; METHYL 4 BROMO 5 (4 ISOPROPOXY 3 METHOXYPHENYL) 1H PYRROLE 2 CARBOXYLATE; METHYL 5 (4 ISOPROPOXY 3 METHOXYPHENYL) 1H PYRROLE 2 CARBOXYLATE; METHYL 5 BROMO 1 (TERT BUTOXYCARBONYL) 1H PYRROLE 2 CARBOXYLATE; NITROGEN; PALLADIUM; UNCLASSIFIED DRUG;

ANNULATION REACTION; ARTICLE; ARYLATION; BROMINATION; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYST; CHEMICAL MODIFICATION; CROSS COUPLING REACTION; CYCLIZATION; DEOXYGENATION; DESULFURIZATION; DRUG SYNTHESIS; ELECTROPHILICITY; LACTONIZATION; NUCLEOPHILICITY; OXIDATION; PROTON NUCLEAR MAGNETIC RESONANCE; PUMMERER REACTION; REGIOSELECTIVE ASSEMBLY; SUZUKI REACTION;

ALKALOIDS; MOLECULAR STRUCTURE; PROLINE; STEREOISOMERISM;

EID: 84896775468     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo402181w     Document Type: Article

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