Syntheses of (+)-complanadine A and lycodine derivatives by regioselective [2 + 2 + 2] cycloadditions

Journal of Organic Chemistry

Volumn 78, Issue 11, 2013, Pages 5647-5668

  Yuan, Changxia ^a   Chang, Chih Tsung ^a   Siegel, Dionicio ^a  

^a UNIVERSITY OF TEXAS AT AUSTIN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOADDITION;

CYCLOADDITION REACTION; CYCLOADDITIONS; DIMERIC ALKALOIDS; GROWTH FACTOR; NEURONAL GROWTH; REGIO-SELECTIVE; RELATED COMPOUNDS; SYNTHETIC ROUTES;

REGIOSELECTIVITY;

1 BENZYL 12 METHYL 8 (QUINOLIN 3 YL) 2,3,4,4A,5,6 HEXAHYDRO 1H 5,10B PROPANO 1,7 PHENANTHROLINE; 1 BENZYL 12 METHYL 8 (THIOPHENE 2 YL) 9 (TRIMETHYLSILYL) 2,3,4,4A,5,6 HEXAHYDRO 1H 5,10B PROPANO 1,7 PHENANTHROLINE; 1 BENZYL 12 METHYL 8 (THIOPHENE 3 YL)2,3,4,4A,5,6 HEXAHYDRO 1H 5,10B PROPANO 1,7 PHENANTHROLINE; 1 BENZYL 12 METHYL 9 (TRIMETHYLSILYL) 8 [(TRIMETHYLSILYL)ETHYNYL] 2,3,4,4A,5,6 HEXAHYDRO 1H 5,10B PROPANO 1,7 PHENANTHROLINE; 1 BENZYL 12 METHYL 9 PHENYL 8 (PYRIDIN 3 YL) 2,3,4,4A,5,6 HEXAHYDRO 1H 5,10B PROPANO 1,7 PHENANTHROLINE; 1 BENZYL 12 METHYL 9 [(TRIMETHYLSILYL)ETHYNYL] 2,3,4,4A,5,6 HEXAHYDRO 1H 5,10B PROPANO 1,7 PHENANTHROLIN; 1 BENZYL 8 (FURAN 2 YL) 12 METHYL 9 (TRIMETHYLSILYL) 2,3,4,4A,5,6 HEXAHYDRO 1H 5,10B PROPANO 1,7 PHENANTHROLINE; 1 BENZYL 9 (TERT BUTYLDIMETHYLSILYL) 8 [(TERT BUTYLDIMETHYLSILYL)ETHYNYL] 12 METHYL 2,3,4,4A,5,6 HEXAHYDRO 1H 5,10B PROPANO 1,7 PHENANTHROLINE; 2 (1 BENZYL 12 METHYL 2,3,4,4A,5,6 HEXAHYDRO 1H 5,10B PROPANO 1,7 PHENANTHROLIN 8 YL)THIAZOLE; 2 (3 AZIDOPROPYL) 5 METHYLCYCLOHEX 2 ENONE; 2 (3 CHLOROPROPYL) 5 METHYL 2 (PHENYLTHIO)CYCLOHEXANONE; 2 (3 CHLOROPROPYL) 5 METHYLCYCLOHEX 2 ENONE; 2 1 (2,4 DIMETHOXYBENZYL) 8A ETHYNYL 7 METHYLDECAHYDROQUINOLIN 5 YL)ACETONITRILE; 2 [1 BENZYL 8A ETHYNYL 7 METHYLDECAHYDROQUINOLIN 5 YL)ACETONITRILE; 2 [2 (3 AZIDOPROPYL) 5 METHYL 3 OXOCYCLOHEXYL)ACETONITRILE; 2 [3 ETHYNYL 2 (3 HYDROXYPROPYL) 3 [(4 METHOXYBENZYL)AMINO] 5 METHYLCYCLOHEXYL]ACETONITRILE; 2 [3 ETHYNYL 3 HYDROXY 2 (3 HYDROXYPROPYL) 5 METHYLCYCLOHEXYL]ACETONITRILE; 2 [3 [(2,4 DIMETHOXYBENZYL)AMINO] 3 ETHYNYL 2 (3 HYDROXYPROPYL) 5 METHYLCYCLOHEXYL]ACETONITRILE; 2 [8A ETHYNYL 1 (4 METHOXYBENZYL) 7 METHYLDECAHYDROQUINOLIN 5 YL]ACETONITRILE; 3 (4 METHYL 6 OXOCYCLOHEX 1 EN 1 YL)PROPYL ACETATE; 3 [2 (BENZYLAMINO) 6 (CYANOMETHYL) 2 ETHYNYL 4 METHYLCYCLOHEXYL]PROPYL ACETATE; 3 [2 (CYANOMETHYL) 4 METHYL 6 OXOCYCLOHEXYL]PROPYL ACETATE; 3 [2 ACETOXY 6 (CYANOMETHYL) 2 ETHYNYL 4 METHYLCYCLOHEXYL]PROPYL ACETATE; 3 [4 METHYL 2 OXO 1 (PHENYLTHIO)CYCLOHEXYL]PROPYL ACETATE; 3 [6 (CYANOMETHYL) 2 ETHYNYL 2 HYDROXY 4 METHYLCYCLOHEXYL]PROPYL ACETATE; 3 [6 (CYANOMETHYL) 2 ETHYNYL 2 [(4 METHOXYBENZYL)AMINO] 4 METHYLCYCLOHEXYL]PROPYL ACETATE; 3 [6 (CYANOMETHYL) 2 [(2,4 DIMETHOXYBENZYL)AMINO] 2 ETHYNYL 4 METHYLCYCLOHEXYL)PROPYL ACETATE; ALKALOID DERIVATIVE; COMPLANADINE A; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ARTICLE; CELLULAR SECRETION; CYCLOADDITION; DRUG SYNTHESIS; GLIA CELL; ISOMER; WITTIG REACTION;

EID: 84879283793     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo400695c     Document Type: Article

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