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Volumn 5, Issue 14, 2003, Pages 2563-2565

Catalyst-controlled inverse-electron-demand hetero-Diels-Alder reactions in the enantio- and diastereoselective synthesis of iridoid natural products

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; CITRONELLAL; CYCLOPENTENE DERIVATIVE; ETHER DERIVATIVE; IRIDOID; NATURAL PRODUCT; SCHIFF BASE; VINYL DERIVATIVE;

EID: 0141630721     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol034883l     Document Type: Article
Times cited : (72)

References (26)
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    • Trost, B. M., Fleming, I., Paquette, L. A., Eds.; Pergamon: Oxford
    • (c) Boger, D. L. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Paquette, L. A., Eds.; Pergamon: Oxford, 1991; Vol. 5, pp 451-512.
    • (1991) Comprehensive Organic Synthesis , vol.5 , pp. 451-512
    • Boger, D.L.1
  • 5
    • 0030797910 scopus 로고    scopus 로고
    • For reviews on iridoid natural products, see: (a) Nangia, A.; Prasuna, G.; Rao, P. B. Tetrahedron 1997, 53, 14507. (b) Thomas A. F.; Bessiere, Y. In Total Synthesis of Natural Products; ApSimon, J., Ed.; Wiley: New York, 1988; Vol. 7, pp 275-454.
    • (1997) Tetrahedron , vol.53 , pp. 14507
    • Nangia, A.1    Prasuna, G.2    Rao, P.B.3
  • 6
    • 85050056091 scopus 로고
    • ApSimon, J., Ed.; Wiley: New York
    • For reviews on iridoid natural products, see: (a) Nangia, A.; Prasuna, G.; Rao, P. B. Tetrahedron 1997, 53, 14507. (b) Thomas A. F.; Bessiere, Y. In Total Synthesis of Natural Products; ApSimon, J., Ed.; Wiley: New York, 1988; Vol. 7, pp 275-454.
    • (1988) Total Synthesis of Natural Products , vol.7 , pp. 275-454
    • Thomas, A.F.1    Bessiere, Y.2
  • 9
    • 0037118895 scopus 로고    scopus 로고
    • As described in this study, complex 5 is isolated as a μ-aquo dimer. However, we report catalyst loadings in terms of the amount of chromium employed, assuming the structure depicted in Scheme 1
    • Gademann, K.; Chavez, D. E.; Jacobsen, E. N. Angew. Chem., Int. Ed. 2002, 41, 3059. As described in this study, complex 5 is isolated as a μ-aquo dimer. However, we report catalyst loadings in terms of the amount of chromium employed, assuming the structure depicted in Scheme 1.
    • (2002) Angew. Chem., Int. Ed. , vol.41 , pp. 3059
    • Gademann, K.1    Chavez, D.E.2    Jacobsen, E.N.3
  • 12
    • 0000679847 scopus 로고    scopus 로고
    • For reviews on the topic of parallel kinetic resolution, see: (a) Kagan, H. Croat. Chem. Acta 1996, 69, 669. (b) Vedejs, E.; Chen, X. J. Am. Chem. Soc. 1997, 119, 2584. (c) Eames, J. Angew. Chem., Int. Ed. 2000, 39, 885.
    • (1996) Croat. Chem. Acta , vol.69 , pp. 669
    • Kagan, H.1
  • 13
    • 0031003909 scopus 로고    scopus 로고
    • For reviews on the topic of parallel kinetic resolution, see: (a) Kagan, H. Croat. Chem. Acta 1996, 69, 669. (b) Vedejs, E.; Chen, X. J. Am. Chem. Soc. 1997, 119, 2584. (c) Eames, J. Angew. Chem., Int. Ed. 2000, 39, 885.
    • (1997) J. Am. Chem. Soc. , vol.119 , pp. 2584
    • Vedejs, E.1    Chen, X.2
  • 14
    • 0034599013 scopus 로고    scopus 로고
    • For reviews on the topic of parallel kinetic resolution, see: (a) Kagan, H. Croat. Chem. Acta 1996, 69, 669. (b) Vedejs, E.; Chen, X. J. Am. Chem. Soc. 1997, 119, 2584. (c) Eames, J. Angew. Chem., Int. Ed. 2000, 39, 885.
    • (2000) Angew. Chem., Int. Ed. , vol.39 , pp. 885
    • Eames, J.1
  • 17
    • 0141442443 scopus 로고
    • Compound 8 has been converted previously into 2, 3 and 4. This work thus constitutes a formal total synthesis of these irodoids. (a) Schaffner, K.; Demuth, M. Chimia 1981, 35, 437. (b) Demuth, M.; Schaffner, K. Angew. Chem., Int. Ed. Engl. 1982, 21, 820.
    • (1981) Chimia , vol.35 , pp. 437
    • Schaffner, K.1    Demuth, M.2
  • 18
    • 0010454813 scopus 로고
    • Compound 8 has been converted previously into 2, 3 and 4. This work thus constitutes a formal total synthesis of these irodoids. (a) Schaffner, K.; Demuth, M. Chimia 1981, 35, 437. (b) Demuth, M.; Schaffner, K. Angew. Chem., Int. Ed. Engl. 1982, 21, 820.
    • (1982) Angew. Chem., Int. Ed. Engl. , vol.21 , pp. 820
    • Demuth, M.1    Schaffner, K.2
  • 25
    • 0141554035 scopus 로고    scopus 로고
    • Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: New York, Chapter 41.4
    • Akutagawa, S. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: New York, 1999; Vol. 3, Chapter 41.4.
    • (1999) Comprehensive Asymmetric Catalysis , vol.3
    • Akutagawa, S.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.