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Volumn 6, Issue 6, 2004, Pages 961-964

Enantioselective total synthesis of eurylene, 14-deacetyl eurylene, and their 11-epimers: The relation between lonophoric nature and cytotoxicity

Author keywords

[No Author keywords available]

Indexed keywords

14 DEACETYLEURYLENE; CYTOTOXIC AGENT; EURYLENE; IONOPHORE; POTASSIUM ION; TETRAHYDROFURAN; TRITERPENE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 12144290138     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol036471i     Document Type: Article
Times cited : (13)

References (27)
  • 4
    • 0027403317 scopus 로고
    • For previous synthetic studies of eurylene, see: (a) Gurjar, M. K.; Saha, U. K. Tetrahedron Lett. 1993, 34, 1833-1836. (b) Molander, G. A.; Swallow, S. J. Org. Chem. 1994, 59, 7148-7151. (c) Ujihara, K.; Shirahama, H. Tetrahedron Lett. 1996, 37, 2039-2042. (d) Morimoto, Y.; Muragaki, K.; Iwai, T.; Morishita, Y.; Kinoshita, T. Angew. Chem., Int. Ed. 2000, 39, 4082-4084.
    • (1993) Tetrahedron Lett. , vol.34 , pp. 1833-1836
    • Gurjar, M.K.1    Saha, U.K.2
  • 5
    • 0028051951 scopus 로고
    • For previous synthetic studies of eurylene, see: (a) Gurjar, M. K.; Saha, U. K. Tetrahedron Lett. 1993, 34, 1833-1836. (b) Molander, G. A.; Swallow, S. J. Org. Chem. 1994, 59, 7148-7151. (c) Ujihara, K.; Shirahama, H. Tetrahedron Lett. 1996, 37, 2039-2042. (d) Morimoto, Y.; Muragaki, K.; Iwai, T.; Morishita, Y.; Kinoshita, T. Angew. Chem., Int. Ed. 2000, 39, 4082-4084.
    • (1994) J. Org. Chem. , vol.59 , pp. 7148-7151
    • Molander, G.A.1    Swallow, S.2
  • 6
    • 0029925757 scopus 로고    scopus 로고
    • For previous synthetic studies of eurylene, see: (a) Gurjar, M. K.; Saha, U. K. Tetrahedron Lett. 1993, 34, 1833-1836. (b) Molander, G. A.; Swallow, S. J. Org. Chem. 1994, 59, 7148-7151. (c) Ujihara, K.; Shirahama, H. Tetrahedron Lett. 1996, 37, 2039-2042. (d) Morimoto, Y.; Muragaki, K.; Iwai, T.; Morishita, Y.; Kinoshita, T. Angew. Chem., Int. Ed. 2000, 39, 4082-4084.
    • (1996) Tetrahedron Lett. , vol.37 , pp. 2039-2042
    • Ujihara, K.1    Shirahama, H.2
  • 7
    • 0034680591 scopus 로고    scopus 로고
    • For previous synthetic studies of eurylene, see: (a) Gurjar, M. K.; Saha, U. K. Tetrahedron Lett. 1993, 34, 1833-1836. (b) Molander, G. A.; Swallow, S. J. Org. Chem. 1994, 59, 7148-7151. (c) Ujihara, K.; Shirahama, H. Tetrahedron Lett. 1996, 37, 2039-2042. (d) Morimoto, Y.; Muragaki, K.; Iwai, T.; Morishita, Y.; Kinoshita, T. Angew. Chem., Int. Ed. 2000, 39, 4082-4084.
    • (2000) Angew. Chem., Int. Ed. , vol.39 , pp. 4082-4084
    • Morimoto, Y.1    Muragaki, K.2    Iwai, T.3    Morishita, Y.4    Kinoshita, T.5
  • 22
    • 1642437445 scopus 로고    scopus 로고
    • note
    • To investigate the conformational difference between 1 and 3, a Monte Carlo conformational search was performed employing the MM2 force field that is included with MacroModel software (v. 6.0). There was no significant conformational difference. The low-energy conformations of 1 and 3 are mainly folded conformations.
  • 27
    • 0017713202 scopus 로고
    • Nonactin and valinomycin exhibited cytotoxicity against KB cells, see: Otake, N.; Sasaki, T. Agric. Biol. Chem. 1977, 41, 1039-1047.
    • (1977) Agric. Biol. Chem. , vol.41 , pp. 1039-1047
    • Otake, N.1    Sasaki, T.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.