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Volumn 61, Issue 20, 1996, Pages 6760-6761

A strategy for total synthesis of complex cardenolides

Author keywords

[No Author keywords available]

Indexed keywords

CARDENOLIDE;

EID: 0029850449     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo961209r     Document Type: Article
Times cited : (41)

References (34)
  • 1
  • 3
    • 84889528549 scopus 로고    scopus 로고
    • For a review of early pioneering partial syntheses see ref 2
    • (a) For a review of early pioneering partial syntheses see ref 2.
  • 4
    • 0000383319 scopus 로고
    • and earlier reviews in this series
    • (b) For reviews of recent partial syntheses, see: Hanson, J. R. Nat. Prod. Rep. 1993, 10, 313 and earlier reviews in this series.
    • (1993) Nat. Prod. Rep. , vol.10 , pp. 313
    • Hanson, J.R.1
  • 5
    • 0028937423 scopus 로고
    • (c) For a recent synthesis of digitoxigenin from an androstane, see: Kabat, M. M. J. Org. Chem. 1995, 60, 1823.
    • (1995) J. Org. Chem. , vol.60 , pp. 1823
    • Kabat, M.M.1
  • 6
    • 0029844604 scopus 로고    scopus 로고
    • in press
    • (a) A total synthesis of digitoxigenin, which represents the first total synthesis of a cardenolide from nonsteroid starting materials, has recently been accomplished: Stork, G.; West, F.; Lee, H. Y.; Isaacs, R. C. A.; Manabe, S. J. Am. Chem. Soc. 1996, 118, in press.
    • (1996) J. Am. Chem. Soc. , vol.118
    • Stork, G.1    West, F.2    Lee, H.Y.3    Isaacs, R.C.A.4    Manabe, S.5
  • 7
    • 16044373297 scopus 로고
    • (b) For total synthesis approaches from nonsteroid starting materials, see: Daniewski, A. R.; Valenta, Z.; White, P. S. Bull. Pol. Acad. Sci., Chem. 1984, 32, 29. Stork, G.; Mook, R. J. Am. Chem. Soc. 1983, 105, 3720. Daniewski, A. R.; Kabat, M. M.; Masnyk, M.; Wicha, J.; Wojciechowska, W. J. Org. Chem. 1988, 53, 4855. Ruel, R.; Deslongchamps, P. Can. J. Chem. 1992, 70, 1939. Rawal, V. H.; Iwasa, S. Abstracts of Papers; 204th National Meeting of the American Chemical Society, Washington, DC; American Chemical Society: Washington, 1992; ORGN 35.
    • (1984) Bull. Pol. Acad. Sci., Chem. , vol.32 , pp. 29
    • Daniewski, A.R.1    Valenta, Z.2    White, P.S.3
  • 8
    • 0000516559 scopus 로고
    • (b) For total synthesis approaches from nonsteroid starting materials, see: Daniewski, A. R.; Valenta, Z.; White, P. S. Bull. Pol. Acad. Sci., Chem. 1984, 32, 29. Stork, G.; Mook, R. J. Am. Chem. Soc. 1983, 105, 3720. Daniewski, A. R.; Kabat, M. M.; Masnyk, M.; Wicha, J.; Wojciechowska, W. J. Org. Chem. 1988, 53, 4855. Ruel, R.; Deslongchamps, P. Can. J. Chem. 1992, 70, 1939. Rawal, V. H.; Iwasa, S. Abstracts of Papers; 204th National Meeting of the American Chemical Society, Washington, DC; American Chemical Society: Washington, 1992; ORGN 35.
    • (1983) J. Am. Chem. Soc. , vol.105 , pp. 3720
    • Stork, G.1    Mook, R.2
  • 9
    • 0023685227 scopus 로고
    • (b) For total synthesis approaches from nonsteroid starting materials, see: Daniewski, A. R.; Valenta, Z.; White, P. S. Bull. Pol. Acad. Sci., Chem. 1984, 32, 29. Stork, G.; Mook, R. J. Am. Chem. Soc. 1983, 105, 3720. Daniewski, A. R.; Kabat, M. M.; Masnyk, M.; Wicha, J.; Wojciechowska, W. J. Org. Chem. 1988, 53, 4855. Ruel, R.; Deslongchamps, P. Can. J. Chem. 1992, 70, 1939. Rawal, V. H.; Iwasa, S. Abstracts of Papers; 204th National Meeting of the American Chemical Society, Washington, DC; American Chemical Society: Washington, 1992; ORGN 35.
    • (1988) J. Org. Chem. , vol.53 , pp. 4855
    • Daniewski, A.R.1    Kabat, M.M.2    Masnyk, M.3    Wicha, J.4    Wojciechowska, W.5
  • 10
    • 0026446754 scopus 로고
    • (b) For total synthesis approaches from nonsteroid starting materials, see: Daniewski, A. R.; Valenta, Z.; White, P. S. Bull. Pol. Acad. Sci., Chem. 1984, 32, 29. Stork, G.; Mook, R. J. Am. Chem. Soc. 1983, 105, 3720. Daniewski, A. R.; Kabat, M. M.; Masnyk, M.; Wicha, J.; Wojciechowska, W. J. Org. Chem. 1988, 53, 4855. Ruel, R.; Deslongchamps, P. Can. J. Chem. 1992, 70, 1939. Rawal, V. H.; Iwasa, S. Abstracts of Papers; 204th National Meeting of the American Chemical Society, Washington, DC; American Chemical Society: Washington, 1992; ORGN 35.
    • (1992) Can. J. Chem. , vol.70 , pp. 1939
    • Ruel, R.1    Deslongchamps, P.2
  • 11
    • 0345613886 scopus 로고
    • 204th National Meeting of the American Chemical Society, Washington, DC; American Chemical Society: Washington, ORGN 35
    • (b) For total synthesis approaches from nonsteroid starting materials, see: Daniewski, A. R.; Valenta, Z.; White, P. S. Bull. Pol. Acad. Sci., Chem. 1984, 32, 29. Stork, G.; Mook, R. J. Am. Chem. Soc. 1983, 105, 3720. Daniewski, A. R.; Kabat, M. M.; Masnyk, M.; Wicha, J.; Wojciechowska, W. J. Org. Chem. 1988, 53, 4855. Ruel, R.; Deslongchamps, P. Can. J. Chem. 1992, 70, 1939. Rawal, V. H.; Iwasa, S. Abstracts of Papers; 204th National Meeting of the American Chemical Society, Washington, DC; American Chemical Society: Washington, 1992; ORGN 35.
    • (1992) Abstracts of Papers
    • Rawal, V.H.1    Iwasa, S.2
  • 13
    • 0001619524 scopus 로고
    • (a) For general reviews of the Heck reaction, see: Heck, R. F. Org. React. (N.Y.) 1982, 27, 345. Meyer, F. E.; de Meijere, A. Angew. Chem., Int. Ed. Engl. 1994, 33, 2379.
    • (1982) Org. React. (N.Y.) , vol.27 , pp. 345
    • Heck, R.F.1
  • 15
    • 84942221470 scopus 로고
    • (b) For recent reviews of aspects of the intramolecular Heck reaction, see: Overman, L. E. Pure Appl. Chem. 1994, 66, 1423. Negishi, E.; Coperet, C.; Ma, S.; Liou, S. Y.; Liu, F. Chem. Rev. 1996, 96, 365.
    • (1994) Pure Appl. Chem. , vol.66 , pp. 1423
    • Overman, L.E.1
  • 16
    • 7044235861 scopus 로고    scopus 로고
    • (b) For recent reviews of aspects of the intramolecular Heck reaction, see: Overman, L. E. Pure Appl. Chem. 1994, 66, 1423. Negishi, E.; Coperet, C.; Ma, S.; Liou, S. Y.; Liu, F. Chem. Rev. 1996, 96, 365.
    • (1996) Chem. Rev. , vol.96 , pp. 365
    • Negishi, E.1    Coperet, C.2    Ma, S.3    Liou, S.Y.4    Liu, F.5
  • 21
    • 84889522785 scopus 로고    scopus 로고
    • note
    • 13C NMR, IR, and MS analysis, while elemental composition was confirmed by combustion analysis or high-resolution mass spectrometry.
  • 22
    • 84889550866 scopus 로고    scopus 로고
    • note
    • Determined by GLC analysis on a Cyclodex B capillary column.
  • 23
    • 84889505592 scopus 로고    scopus 로고
    • note
    • The ee of 5 was 96-98% when 0.5 equiv of oxazaborolidine 4 was employed.
  • 25
    • 0001997183 scopus 로고
    • (b) For a recent review of the Ireland-Claisen rearrangement, see: Pereira, S.; Srebnik, M. Aldrichim. Acta 1993, 26, 17.
    • (1993) Aldrichim. Acta , vol.26 , pp. 17
    • Pereira, S.1    Srebnik, M.2
  • 34
    • 84889502288 scopus 로고    scopus 로고
    • note
    • Crystallographic data for this intermediate have been deposited with the Cambridge Crystallographic Data Centre. The coordinates can be obtained, on request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, UK.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.