Large-scale synthesis of SB-462795, a cathepsin K inhibitor: the RCM-based approaches

Tetrahedron

Volumn 65, Issue 32, 2009, Pages 6291-6303

  Wang, Huan ^a   Matsuhashi, Hayao ^a   Doan, Brian D ^a   Goodman, Steven N ^a   Ouyang, Xi ^a   Clark Jr , William M ^a  

^a GLAXOSMITHKLINE   (United States)

Author keywords

Curtius; Epoxide opening; Oxazolidinone cleavage; RCM

Indexed keywords

1,2,3 TRIDEOXY 3 (1,3 DIOXO 1,3 DIHYDRO 2H ISOINDOL 2 YL) 5 O [(4 METHYLPHENYL)SULFONYL] LEVO THREO PENT 1 ENITOL; 1,3,4,5 TETRADEOXY 3 (1,3 DIOXO 1,3 DIHYDRO 2H ISOINDOL 2 YL) 1 [[1 METHYL 2 PROPEN 1 YL](2 PYRIDINYLSULFONYL)AMINO] LEVO THREO PENT 4 ENITOL; 2 [3 HYDROXY 7 METHYL 1 (2 PYRIDINYLSULFONYL)2,3,4,7 TETRAHYDRO 1H AZEPIN 4 YL] 1H ISOINDOLE 1,3(2H) DIONE; 2 [3 HYDROXY 7 METHYL 1 (2 PYRIDINYLSULFONYL)HEXAHYDRO 1H AZEPIN 4 YL] 1H ISOINDOLE 1,3(2H) DIONE; 3 (2 BUTENOYL) 4 PHENYL 1,3 OXAZOLIDIN 2 ONE; 3 [3 HYDROXY 7 METHYL 1 (2 PYRIDINYLSULFONYL) 2,3,4,7 TETRAHYDRO 1H AZEPIN 4 YL] 4 PHENYL 1,3 OXAZOLIDIN 2 ONE; 4 AMINO 7 METHYL 1 (2 PYRIDINYLSULFONYL) HEXAHYDRO 1H AZEPIN 3 OL; 4 AMINO 7 METHYL 1 (2 PYRINDINYLSULFONYL) 2,3,4,7 TETRAHYDRO 1H AZEPIN 3 OL; 4,5 ANHYDRO 1,2,3 TRIDEOXY 3 (1,3 DIOXO 1,3 DIHYDRO 2H ISOINDOL 2 YL) LEVO THREO PENT 1 ENITOL; 6 METHYL 5 (2 PYRIDINYLSULFONYL) 1,3A,4,5,6,8A HEXAHYDRO 2H (1,3)OXAZOLOL(5,4-C)AZEPIN 2 ONE; 6 METHYL 5 (2 PYRIDINYLSULFONYL) OCTAHYDRO 2H (1,3)OXAZOLO(5,4-C)AZEPIN 2 ONE; AMINOALCOHOL; CARBON; METHANOL; N (1 BENZOFURAN 2 YLCARBONYL) LEUCINE; N (1 METHYL 2 PROPEN 1 YL) 2 PYRIDINESULFONAMIDE; N (1 METHYL 2 PROPEN 1 YL) N (2 OXOETHYL) 2 PYRIDINESULFONAMIDE; N [(4 ETHENYL 2 OXO 1,3 OXAZOLIDIN 5 YL)METHYL] N (1 METHYL 2 PROPEN 1 YL) 2 PYRIDINESULFONAMIDE; N [(4 ETHYL 2 OXO 2,3 DIHYDRO 1,3 OXAZOL 5 YL)METHYL] N (1 METHYL 2 PROPEN 1 YL) 2 PYRIDINESULFONAMIDE; N [1 [[[3 HYDROXY 7 METHYL 1 (2 PYRIDINYLSULFONYL)HEXAHYDRO 1H AZEPIN 4 YL] AMINO]CARBONYL] 3 METHYLBUTYL] 1 BENZOFURAN 2 CARBOXAMIDE; N [2 HYDROXY 3 [[(2 OXO 4 PHENYL 1,3 OXAZOLIDIN 3 YL)CARBONYL] 4 PENTEN 1 YL] N 1 METHYL 2 PROPEN 1 YL] 2 PYRIDINESULFONAMIDE; N [3 (HYDRAZINOCARBONYL) 2 HYDROXY 4 PENTEN 1 YL] N (1 METHYL 2 PROPEN 1 YL) 2 PYRIDINESULFONAMIDE; RELACATIB; SULFONAMIDE; UNCLASSIFIED DRUG;

ALDOL REACTION; ARTICLE; DRUG OXIDATION; DRUG STRUCTURE; DRUG SYNTHESIS; LARGE SCALE PRODUCTION; PRIORITY JOURNAL; RING CLOSING METATHESIS; SCALE UP; STEREOCHEMISTRY;

EID: 67649587136     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2009.06.022     Document Type: Article

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