Development of a Brønsted acid-promoted arene-ynamide cyclization toward the total syntheses of marinoquinolines A and C and aplidiopsamine A

Journal of Organic Chemistry

Volumn 80, Issue 2, 2015, Pages 957-964

  Yamaoka, Yousuke ^a   Yoshida, Takahiro ^a   Shinozaki, Makiko ^a   Yamada, Ken Ichi ^a   Takasu, Kiyosei ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BROMINE; REACTION INTERMEDIATES; SUBSTITUTION REACTIONS;

CHEMICAL EQUATIONS; ELECTROPHILIC AROMATIC SUBSTITUTIONS; FACILE ACCESS; HIGH YIELD; TOTAL SYNTHESIS;

CYCLIZATION;

3H PYRROLO[2,3 C]QUINOLINE; 4 [(TRIISOPROPYLSILYL)METHYL] 3H PYRROLO[2,3 C]QUINOLINE; APLIDIOPSAMINE A; BRONSTED ACID; MARINOQUINOLINE A; MARINOQUINOLINE C; POLYCYCLIC AROMATIC HYDROCARBON; QUINOLINE DERIVATIVE; TERT BUTYL (2 BROMO 5 METHYLPHENYL)CARBAMATE; TERT BUTYL 3 [2 [( TERT BUTOXYCARBONYL)AMINO]PHENYL] 1H INDOLE 1 CARBOXYLATE; TERT BUTYL 3 [2 [( TERT BUTOXYCARBONYL)[(TRIISOPROPYLSILYL)ETHYNYL]AMINO]PHENY] 1H PYRROLE 1 CARBOXYLATE; TERT BUTYL 3 [2 [(BROMOETHYNYL)(TERT BUTOXYCARBONYL)AMINO]PHENYL] 1H PYRROLE 1 CARBOXYLATE; TERT BUTYL 3 [2 [(TERT BUTOXYCARBONYL)(3 ETHOXY 3 OXOPROP 1 YN 1 YL)AMINO]PHENYL] 1H PYRROLE 1 CARBOXYLATE; TERT BUTYL 3 [2 [(TERT BUTOXYCARBONYL)(CHLOROETHYNYL)AMINO]PHENYL] 1H PYRROLE 1 CARBOXYLATE; TERT BUTYL 3 [2 [(TERT BUTOXYCARBONYL)(ETHYNYL)AMINO]PHENYL] 1H PYRROLE 1 CARBOXYLATE; TERT BUTYL 3 [2 [(TERT BUTOXYCARBONYL)(PHENYLETHYNYL)AMINO]PHENYL] 1H PYRROLE 1 CARBOXYLATE; TERT BUTYL 3 [2 [(TERT BUTOXYCARBONYL)AMINO] 4 FLUOROPHENYL] 1H PYRROLE 1 CARBOXYLATE; TERT BUTYL 3 [2 [(TERT BUTOXYCARBONYL)AMINO] 4 METHYLPHENYL] 1H PYRROLE 1 CARBOXYLATE; TERT BUTYL 3 [2 [(TERT BUTOXYCARBONYL)AMINO]PHENYL] 1H PYRROLE 1 CARBOXYLATE; TERT BUTYL 3 [2 [(TERT BUTOXYCARBONYL)[(TRIISOPROPYLSILYL) ETHYNYL]AMINO] 4 FLUOROPHENYL] 1H PYRROLE 1 CARBOXYLATE; TERT BUTYL 3 [2 [(TERT BUTOXYCARBONYL)[(TRIISOPROPYLSILYL) ETHYNYL]AMINO] 4 METHYLPHENYL] 1H PYRROLE 1 CARBOXYLATE; TERT BUTYL 3 [2 [(TERT BUTOXYCARBONYL)[(TRIISOPROPYLSILYL)ETHYNYL]AMINO]PHENYL] 1H INDOLE 1 CARBOXYLATE; TERT BUTYL [1,1 BIPHENYL] 2 YL[(TRIISOPROPYLSILYL)ETHYNYL] CARBAMATE; TERT BUTYL [1,1' BIPHENYL] 2 YLCARBAMATE; TERT BUTYL [2 (FURAN 3 YL)PHENYL]CARBAMATE; TERT BUTYL [2 (FURAN 3 YL)PHENYL][(TRIISOPROPYLSILYL)ETHYNYL] CARBAMATE; TERT BUTYL [2 (THIOPHEN 3 YL)PHENYL]CARBAMATE; TERT BUTYL [2 (THIOPHEN 3 YL)PHENYL][(TRIISOPROPYLSILYL)ETHYNYL]CARBAMATE; UNCLASSIFIED DRUG; UNINDEXED DRUG; [1 (TERT BUTOXYCARBONYL) 1H PYRROL 3 YL]BORONIC ACID; ACID; PYRROLE DERIVATIVE;

ARTICLE; COLUMN CHROMATOGRAPHY; CYCLIZATION; DRUG SYNTHESIS; ELECTROPHILICITY; ELECTROSPRAY MASS SPECTROMETRY; PROTON NUCLEAR MAGNETIC RESONANCE; RING OPENING; ROOM TEMPERATURE; SUBSTITUTION REACTION; THIN LAYER CHROMATOGRAPHY; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; SYNTHESIS;

ACIDS; CATALYSIS; CYCLIZATION; MOLECULAR STRUCTURE; PYRROLES; QUINOLINES;

EID: 84921301852     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo502467m     Document Type: Article

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