Macrolactamization versus macrolactonization: Total synthesis of FK228, the depsipeptide histone deacetylase inhibitor

Journal of Organic Chemistry

Volumn 73, Issue 23, 2008, Pages 9353-9361

  Wen, Shijun ^a   Packham, Graham ^b   Ganesan, A ^a  

^a UNIVERSITY OF SOUTHAMPTON   (United Kingdom)

^b UNIVERSITY OF SOUTHAMPTON   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ACIDS; AMIDES; BIOCHEMICAL ENGINEERING; CARBOXYLIC ACIDS; CHEMICAL BONDS; CHEMICAL REACTIONS; ESTERIFICATION; ESTERS; ORGANIC ACIDS; ORGANIC COMPOUNDS;

ALLYLIC ALCOHOLS; AMIDE BONDS; ANTI CANCER AGENTS; CHEMICAL EQUATIONS; CLINICAL TRIALS; CYCLIC DEPSIPEPTIDE; EARLY STAGES; ESTER BONDS; HISTONE DEACETYLASE INHIBITORS; HYDROXY ACIDS; MACROCYCLIZATION; MACROCYLIZATION; MACROLACTAMIZATION; MACROLACTONIZATION; NATURAL PRODUCTS; STERIC HINDRANCES; TOTAL SYNTHESES;

SYNTHESIS (CHEMICAL);

(4,3) 3 HYDROXY 7 MERCAPTO [S TRIPHENYLMETHYL] 4 HEPTENOIC ACID; 2 [2 (9H FLUOREN 9 YLMETHOXYCARBONYLAMINO) 3 TRITYLSULFANYL PROPIONYLAMINO] 3 HYDROXY BUTYRIC ACID METHYL ESTER; 2 [2 [2 (9H FLUOREN 9 YLMETHOXYCARBONYLAMINO) 3 METHYL BUTYRYLAMINO] 3 TRITYLSULFANYL PROPIONYLAMINO] 3 HYDROXY BUTYRIC ACID METHYL ESTER; 2 [2 [2 (9H FLUOREN 9 YLMETHOXYCARBONYLAMINO) 3 METHYL BUTYRYLAMINO] 3 TRITYLSULFANYL PROPIONYLAMINO]BUT 2 ENOIC ACID METHYL ESTER; 2 [2 [2 AMINO 3 METHYL BUTYRYLAMINO] 3 TRITYLSULFANYL PROPIONYLAMINO]BUT 2 ENOIC ACID METHYL ESTER; 2 [2 [2 [2 (9H FLUOREN 9 YLMETHOXYCARBONYLAMINO) 3 METHYL BUTYRYLAMINO] 3 TRITYLSULFANYL PROPIONYLAMINO] BUT 2 ENOYLAMINO] 3 METHYL BUTYRIC ACID; 3 HYDROXY 7 TRITYLSULFANYL HEPT 4 ENOIC ACID 2 TRIMETHYLSILANYL ETHYL ESTER; 3 [2 [2 [2 [2 (9H FLUOREN 9 YLMETHOXYCABONYLAMINO) 3 METHYL BUTYRYLAMINO] 3 TRITYLSULFANYL PROPIONYLAMINO]BUT 2 ENOYLAMINO] 3 METHYL BUTYRYLOXY] 7 [2 ETH YLIDENE 1,1 DIPHENYL HEXA 3,5 DIENYLSULFANYL]HEPT 4 ENOIC ACID 2 TRIMETHL SILANYL ETHYL ESTER; 3 [2 [2 [2 [2 (9H FLUOREN 9 YLMETHOXYCARBONYLAMINO) 3 METHYL BUTYRYLAMINO] 3 TRITYLSULFANYL PROPIONYLAMINO]BUT 2 ENOYLAMINO] 3 METHYL BUTYRYLOXY] 7 [2 ETH YLIDENE 1,1 DIPHENYL HEXA 3,5 DIENYLSULFANYL]HEPT 4 ENOIC ACID 2 TRIMETHYLSILANYL ETHYL ESTER; 6 ETH YLIDENE 3,12 DIISOPROPYL 16 [4 TRITYLSULFANYL BUT 1 ENYL] 9 TRITYLSULFANYLMETHYL 1 OXA 4,7,10,13 TETRAAZACYCLOHEXADECANE 2,5,8,11,14 PENTAONE; 7 ETH YLIDENE 4,21 DIISOPROPYL 2 OXA 12,13 DITHIA 5,8,20,23 TETRAAZA BICYCLO[8.7.8]TRICOS 16 ENE 3,6,9,19,22 PENTAONE; 7 [2 ETHYLIDENE 1,1 DIPHENYL HEXA 3,5 DIENYLSULFANYL] 3 [2 (9H FLUOREN 9 YLMETHOXYCARBONYLAMINO) 3 METHYLBUTYLRYLOXY]HEPT 4 ENOIC ACID 2 TRIMETHYLSILANYL ETHYL ESTER; ALLYL COMPOUND; AMIDE; ANTINEOPLASTIC AGENT; CARBOXYLIC ACID; DEPSIPEPTIDE; ESTER; HISTONE DEACETYLASE INHIBITOR; HYDROXYACID; ROMIDEPSIN; UNCLASSIFIED DRUG; ALCOHOL DERIVATIVE; ANTINEOPLASTIC ANTIBIOTIC; LACTONE; PEPTIDE;

ARTICLE; CHEMICAL BINDING; CHEMICAL MODIFICATION; CHEMICAL STRUCTURE; CROSS LINKING; ESTERIFICATION; FERMENTATION; MACROLACTAMIZATION; MACROLACTONIZATION; STRUCTURE ACTIVITY RELATION; SYNTHESIS; CHEMICAL MODEL; CHEMISTRY; DRUG DESIGN; MEDICINAL CHEMISTRY; ORGANIC CHEMISTRY; PROCEDURES;

ALCOHOLS; ANTIBIOTICS, ANTINEOPLASTIC; CARBOXYLIC ACIDS; CHEMISTRY, ORGANIC; CHEMISTRY, PHARMACEUTICAL; DEPSIPEPTIDES; DRUG DESIGN; HISTONE DEACETYLASE INHIBITORS; LACTONES; MODELS, CHEMICAL; PEPTIDES;

EID: 57449108068     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo801866z     Document Type: Article

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