Toward the total synthesis of (±)-andrastin C

Journal of Organic Chemistry

Volumn 78, Issue 1, 2013, Pages 93-103

  Okamoto, Rei ^a   Takeda, Kazutaka ^c   Tokuyama, Hidetoshi ^a   Ihara, Masataka ^b   Toyota, Masahiro ^c  

^a TOHOKU UNIVERSITY   (Japan)

^b HOSHI UNIVERSITY   (Japan)

^c Osaka Prefecture University   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CARBON FRAMEWORK; CARBONYL-ENE REACTIONS; FUNCTIONALIZED; INTRAMOLECULAR DIELS-ALDER REACTION; PROPANAL; STEREO-SELECTIVE; SYNTHETIC ROUTES; TOTAL SYNTHESIS;

CHEMISTRY;

ORGANIC COMPOUNDS;

2 (BENZYLOXYL) 8 [(BENZYLOXY)METHYL] 8 [2 (METHOXYMETHOXY) 3 BUTENYL] 1,2,3,4,4A,4B,5,8,8A,9,10,10A DODECAHYDRO 1,1,4A,6,7,8A HEXAMETHYLPHENANTHRENE; 2 (TERT BUTYLDIMETHYLSILOXY) 8,8 (ETHYLENEDIOXYL) 1,4A,8A TRIMETHYL 3,4,4A,4B,5,6,7,8,8A,9,10,10A DODECAHYDROPHENANTHRENE; 2 [(TERT BUTYLDIMETHYLSILYL)OXY] 8,8 (ETHYLENEDIOXY) 1,4A,8A TRIMETHYL 1,2,3,4,4A,4B,5,6,7,8,8A,9,10,10A TETRADECAHYDROCYCLOPENTA[A]PHENANTHRENE; 3 (BENZYLOXY) 14 [(BENZYLOXY)METHYL] 1,3,4,5,6,7,8,9,70,15,16 DECAHYDRO 4,4,8,10,12,13 HEXAMETHYLCYCLOPENTA[A]PHENANTHREN 17 ONE; 4 [(BENZYLOXY)METHYL] 9A (TERT BUTYLDIMETHYL) 1,1A,1B,2,3,3A,7,7A,7B,8,9,9A DODECAHYDRO 1A,3A,5,7B TETRAMETHYLCYCLOPROPA[A]PHENANTHREN 6 ONE; 4 [(BENZYLOXYL)METHYL] 9A [(TERT BUTYLDIMETHYLSILYL)OXYL] 1A,1B,2,3,3A,4,7,7A,7B,8,9,9A DODECAHYDRO 1A,3A,5,7B TETRAMETHYLCYCLOPROPA[A]PHENANTHREN 4 ONE; 5 [6 ISOPROPENYL 2,2 (ETHYLENEDIOXY) 1 METHYLCYCLOHEXYL] 3 METHYL 2 [(TERT BUTYLDIMETHYLSILYL)OXYL] 1,3 HEXADIENE; 6 [6 ISOPROPENYL 2,2 (ETHYLENEDIOXY) 1 METHYLCYCLOHEXYL] 3 METHYL 3 HEXEN 2 ONE; 6,6 ETHYLENEDIOXY 1,1,5A TRIMETHYL 4,5,5A,6,7,8,9,9A OCTAHYDRO 2 BENZ[C]OXEPIN 3 ONE; 7 (BENZYLOXYL) 1 [(BENZYLOXY)METHYL] 1 [2 [(TERT BUTYLDIMETHYLSILYL)OXY]ETHYL] 1,4,4A,4B,5,6,7,8,8A,9,10,10A DODECAHYDRO 2,3,4B,8,8,10 HEXAMETHYLPHENANTHRENE; 7 (BENZYLOXYL) 1 [(BENZYLOXY)METHYL] 1,4,4A,4B,5,6,7,8,8A,9,10,10A DODECAHYDRO 1 (2 HYDROXYETHYL) 2,4,4B,8,8,10A PENTAMETHYLPHENANTHRENE; 7 (BENZYLOXYL) 1 [(BENZYLOXY)METHYL] 1,4,4A,4B,5,6,7,8,8A,9,10,10A DODECAHYDRO 2,3,4B,8,8,10A HEXAMETHYLPHENANTHREN 1 YL]ACETALDEHYDE; 7 (BENZYLOXYL) 1 [(BENZYLOXY)METHYL] 3,4,4A,4B,5,6,7,8,8A,9,10,10A DODECAHYDRO 2,4B,8,8,10A PENTAMETHYLPHENANTHREN 3 OL; 7 (BENZYLOXYL) 1 [(BENZYLOXY)METHYL] 3,4,4A,4B,5,6,7,8,8A,9,10,10A DODECHAHYDRO 2,4B,8,8,10A PENTAMETHYLPHENANTHREN 3 OL; 7 (BENZYLOXYL) 1 [(BENZYLOXY)METHYL] TETRADECAHYDRO 1 (2 HYDROXYETHYL) 2,4B,8,8,10A PENTAMETHYLPHENANTHREN 3 OL; 8 [(BENZYLOXY)METHYL] 4,4A,4B,5,6,7,8,8A,9,10,10A DECAHYDRO 7 HYDROXY 2,4B,8,8,10A PENTAMETHYLPHENANTHRENE 3 ONE; 8 [(BENZYLOXY)METHYL] 4,4A,4B,5,8A,9,10,10A OCTAHYDRO 1,1,4A,7,8A PENTAMETHYLPHENANTHRENE 2,6 DIONE; 8,8 (ETHYLENEDIOXY) 1,4A,8A TRIMETHYL 1,2,3,4,4A,4B,5,6,7,8,8A,9,10,10A TETRADECAHYDROPHENANTHRENE 2 ONE; 9A [(TERT BUTYLDIMETHYLSILYL)OXYL] 1,1A,1B,2,3,3A,7,7A,7B,8,9,9A DODECAHYDRO 1A,3A,5,7B TETRAMETHYLCYCLOPROPA[A]PHENANTHREN 4 ONE; 9A [(TERT BUTYLDIMETHYLSILYL)OXYL] 1,2,3,4,4A,4B,5,6,7,8,A,9,10,10A TERTADECAHYDRO 1A,3A,7B TRIMETHYLCYCLOPROPA[A]PHENANTHREN 4 ONE; ANDRASTIN C; CARBONYL DERIVATIVE; METHYL 3 [(1 HYDROXY 1 METHYLETHYL) 2,2 (ETHYLENEDIOXY) 1 METHYLCYCLOHEXYL]PROPANOATE; METHYL 3 [6 ISOPROPENYL 2,2 (ETHYLENEDIOXY) 1 METHYLCYCLOHEXYL]PROPANOATE; PHENANTHRENE DERIVATIVE; PROPANOLAMINE DERIVATIVE; PROTEIN FARNESYLTRANSFERASE INHIBITOR; UNCLASSIFIED DRUG;

ARTICLE; COLUMN CHROMATOGRAPHY; DIELS ALDER REACTION; DRUG SYNTHESIS; STEREOCHEMISTRY;

ANDROSTADIENES; MOLECULAR STRUCTURE; PHENANTHRENES; STEREOISOMERISM;

EID: 84874076582     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo301948h     Document Type: Article

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