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Volumn 38, Issue 23, 1999, Pages 3545-3547

Asymmetric total synthesis of fluvirucinine A1

Author keywords

Alkaloids; Antiviral agents; Natural products; Rearrangements; Total synthesis

Indexed keywords

ANTIVIRUS AGENT; BETA LACTAM ANTIBIOTIC; FLUVIRUCININE A; UNCLASSIFIED DRUG;

EID: 0033521185     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(19991203)38:23<3545::AID-ANIE3545>3.0.CO;2-0     Document Type: Article
Times cited : (65)

References (29)
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    • d) B. M. Trost, M. A. Ceschi, B. Konig, Angew. Chem. 1997, 109, 1562; Angew. Chem. Int. Ed. Engl. 1997, 36, 1486.
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    • note
    • [3d]
  • 16
    • 0018777888 scopus 로고
    • To the best of our knowledge, our procedure is the first direct diastereoselective vinylation at a lactam carbonyl group. The reported cyanide addition to a lactam carbonyl group and the subsequent substitution by a vinyl group was not adopted, because partial epimerization during the cyanide addition was consistently observed: R. D. Gless, H. Rapoport, J. Org. Chem. 1979, 44, 1324; M. Rubiralta, E. Giralt, A. Diez, Piperidine, Elsevier, New York, 1991, pp 235-244;
    • (1979) J. Org. Chem. , vol.44 , pp. 1324
    • Gless, R.D.1    Rapoport, H.2
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    • 0012810872 scopus 로고
    • Elsevier, New York
    • To the best of our knowledge, our procedure is the first direct diastereoselective vinylation at a lactam carbonyl group. The reported cyanide addition to a lactam carbonyl group and the subsequent substitution by a vinyl group was not adopted, because partial epimerization during the cyanide addition was consistently observed: R. D. Gless, H. Rapoport, J. Org. Chem. 1979, 44, 1324; M. Rubiralta, E. Giralt, A. Diez, Piperidine, Elsevier, New York, 1991, pp 235-244;
    • (1991) Piperidine , pp. 235-244
    • Rubiralta, M.1    Giralt, E.2    Diez, A.3
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    • b) M. Yamaguchi, I. Hirao, Tetrahedron Lett. 1983, 24, 1719; Y. C. Hwang, M. Chu, F. W. Fowler, J. Org. Chem. 1985, 50, 3885;
    • (1983) Tetrahedron Lett. , vol.24 , pp. 1719
    • Yamaguchi, M.1    Hirao, I.2
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    • For related examples, see M. J. Fisher, L. E. Overman, J. Org. Chem. 1990, 55, 1447; T. Hosaka, Y. Torisawa, M. Nakagawa, Tetrahedron Lett. 1997, 38, 3535.
    • (1990) J. Org. Chem. , vol.55 , pp. 1447
    • Fisher, M.J.1    Overman, L.E.2
  • 29
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    • note
    • [1c] We thank Professor Takenori Kusumi of Tokushima University and Professor Hiroshi Kakisawa of the University of Tsukuba for kindly providing spectral data of the fluvirucins.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.