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Volumn 53, Issue 28, 1997, Pages 9611-9622

Synthesis of a chiral 1β-methylcarbapenem key intermediate using radical cyclization of N-vinylic α-bromo amides

Author keywords

[No Author keywords available]

Indexed keywords

1BETA METHYLCARBAPENEM; 2 [3 [1 (TERT BUTYLDIMETHYLSILOXY)ETHYL] 4 OXOAZETIDIN 2 YL]PROPANOATE METHYL ESTER; 3 ACETOXY 2 BROMO N [2 (3 METHOXYPHENYL) 1 PROPEN 1 YL] N (1 PHENYLETHYL)BUTANAMIDE; BROMINE DERIVATIVE; CARBAPENEM DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0030793266     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)00645-5     Document Type: Article
Times cited : (30)

References (22)
  • 1
    • 84990135406 scopus 로고
    • For reviews on the stereochemical control in radical addition and cyclization reactions, see: Giese, B. Angew. Chem. Int. Ed. Engl. 1989, 25, 969. RajanBabu, T.V. Acc. Chem. Res. 1991, 24, 139. Porter, N.A.; Giese, B.; Curran, D.P. Acc. Chem. Res. 1991, 24, 296. Smadja, W. Synlett 1994, 1.
    • (1989) Angew. Chem. Int. Ed. Engl. , vol.25 , pp. 969
    • Giese, B.1
  • 2
    • 0010720585 scopus 로고
    • For reviews on the stereochemical control in radical addition and cyclization reactions, see: Giese, B. Angew. Chem. Int. Ed. Engl. 1989, 25, 969. RajanBabu, T.V. Acc. Chem. Res. 1991, 24, 139. Porter, N.A.; Giese, B.; Curran, D.P. Acc. Chem. Res. 1991, 24, 296. Smadja, W. Synlett 1994, 1.
    • (1991) Acc. Chem. Res. , vol.24 , pp. 139
    • RajanBabu, T.V.1
  • 3
    • 12044254102 scopus 로고
    • For reviews on the stereochemical control in radical addition and cyclization reactions, see: Giese, B. Angew. Chem. Int. Ed. Engl. 1989, 25, 969. RajanBabu, T.V. Acc. Chem. Res. 1991, 24, 139. Porter, N.A.; Giese, B.; Curran, D.P. Acc. Chem. Res. 1991, 24, 296. Smadja, W. Synlett 1994, 1.
    • (1991) Acc. Chem. Res. , vol.24 , pp. 296
    • Porter, N.A.1    Giese, B.2    Curran, D.P.3
  • 4
    • 85034533375 scopus 로고
    • For reviews on the stereochemical control in radical addition and cyclization reactions, see: Giese, B. Angew. Chem. Int. Ed. Engl. 1989, 25, 969. RajanBabu, T.V. Acc. Chem. Res. 1991, 24, 139. Porter, N.A.; Giese, B.; Curran, D.P. Acc. Chem. Res. 1991, 24, 296. Smadja, W. Synlett 1994, 1.
    • (1994) Synlett , pp. 1
    • Smadja, W.1
  • 9
    • 0030028910 scopus 로고    scopus 로고
    • For a review on the synthesis of 1β-methylcarbapenem key intermediates, see: Berks, A.H. Tetrahedron 1996, 52, 331. For recent leading references, see: (a) Sakurai, O.; Ogiku, T.; Takahashi, M.; Horikawa, H.; Iwasaki, T. Tetrahedron Lett. 1994, 55, 2187.
    • (1996) Tetrahedron , vol.52 , pp. 331
    • Berks, A.H.1
  • 10
    • 0028355311 scopus 로고
    • For a review on the synthesis of 1β-methylcarbapenem key intermediates, see: Berks, A.H. Tetrahedron 1996, 52, 331. For recent leading references, see: (a) Sakurai, O.; Ogiku, T.; Takahashi, M.; Horikawa, H.; Iwasaki, T. Tetrahedron Lett. 1994, 55, 2187.
    • (1994) Tetrahedron Lett. , vol.55 , pp. 2187
    • Sakurai, O.1    Ogiku, T.2    Takahashi, M.3    Horikawa, H.4    Iwasaki, T.5
  • 21
    • 0342520611 scopus 로고    scopus 로고
    • note
    • Miura and Choi also reported independently that the substitution of a large TBDMS group on the nitrogen atom of β-lactam led to the diastereoselective deallyloxycarbonylation and decarboxylation at the C-4 side chain to give desired 1β-methyl derivatives, respectively. See refs. 3b, 3c and 3g.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.