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Volumn 68, Issue 19, 2003, Pages 7143-7157

Strategic use of pinacol-terminated prins cyclizations in target-oriented total synthesis

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; SYNTHESIS (CHEMICAL);

EID: 0141678121     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo034982c     Document Type: Review
Times cited : (244)

References (173)
  • 3
    • 0141746783 scopus 로고    scopus 로고
    • Breslow, R. C. D., Tirrell, M. V., Eds.; National Academy Press: Washinton; Chapters 3, 4, 7, 8, 10, 11
    • See, for example: Beyond the Molecular Frontier: Challenges for Chemistry and Chemical Engineering; Breslow, R. C. D., Tirrell, M. V., Eds.; National Academy Press: Washinton, D.C., 2003; Chapters 3, 4, 7, 8, 10, 11.
    • (2003) Beyond the Molecular Frontier: Challenges for Chemistry and Chemical Engineering
  • 4
    • 0003417469 scopus 로고
    • Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford
    • (a) Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vols. 1-9.
    • (1991) Comprehensive Organic Synthesis , vol.1-9
  • 5
    • 0003579939 scopus 로고
    • Paquette, L. A., Ed.; Wiley & Sons: New York
    • (b) Encyclopedia of Reagents for Organic Synthesis; Paquette, L. A., Ed. ; Wiley & Sons: New York, 1995; Vols. 1-8.
    • (1995) Encyclopedia of Reagents for Organic Synthesis , vol.1-8
  • 6
    • 7044235263 scopus 로고    scopus 로고
    • For recent reviews, see: (a) Tietze, L. F. Chem. Rev. 1996, 96, 115-136.
    • (1996) Chem. Rev. , vol.96 , pp. 115-136
    • Tietze, L.F.1
  • 11
    • 0000770422 scopus 로고    scopus 로고
    • (f) Wang, K. K. Chem. Rev. 1996, 96, 207-222.
    • (1996) Chem. Rev. , vol.96 , pp. 207-222
    • Wang, K.K.1
  • 20
    • 0000997425 scopus 로고
    • Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford
    • For brief reviews, see: (a) Overman, L. E.; Ricca, D. J. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 2, pp 1007-1010.
    • (1991) Comprehensive Organic Synthesis , vol.2 , pp. 1007-1010
    • Overman, L.E.1    Ricca, D.J.2
  • 30
    • 0141746780 scopus 로고
    • For subsequent investigations by the Mousset group, see: (a) Mousset, G. Bull. Soc. Chim. Fr. 1971, 4097-4106.
    • (1971) Bull. Soc. Chim. Fr. , pp. 4097-4106
    • Mousset, G.1
  • 40
    • 0001928999 scopus 로고
    • NATO ASI Series C; Schinzer, D., Ed.; Kluwer Academic: Dordrecht, The Netherlands
    • For brief reviews, see ref 9b,c and: Overman, L. E. In Selectivities in Lewis Acid-Promoted Reactions; NATO ASI Series C; Schinzer, D., Ed.; Kluwer Academic: Dordrecht, The Netherlands, 1989; Vol. 289, pp 1-20.
    • (1989) Selectivities in Lewis Acid-Promoted Reactions , vol.289 , pp. 1-20
    • Overman, L.E.1
  • 48
    • 0004117577 scopus 로고
    • American Chemical Society: Washington, D.C.; Chapters 2 and 3
    • For discussions of the barriers of C-C single bond rotations, see: (a) Eliel, E. L.; Allinger, N. L.; Angyal, S. J.; Morrison, G. A. Conformational Analysis; American Chemical Society: Washington, D.C., 1965; Chapters 2 and 3.
    • (1965) Conformational Analysis
    • Eliel, E.L.1    Allinger, N.L.2    Angyal, S.J.3    Morrison, G.A.4
  • 53
    • 0030768660 scopus 로고    scopus 로고
    • For discussions of electrophilic additions to chiral allylic ethers, see: (a) Haller, J.; Strassner, T.; Houk, K. N. J. Am. Chem. Soc. 1997, 119, 8031-8034.
    • (1997) J. Am. Chem. Soc. , vol.119 , pp. 8031-8034
    • Haller, J.1    Strassner, T.2    Houk, K.N.3
  • 59
    • 0001290261 scopus 로고
    • Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford
    • For a comprehensive review, see: Snider, B. B. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 2, pp 527-562.
    • (1991) Comprehensive Organic Synthesis , vol.2 , pp. 527-562
    • Snider, B.B.1
  • 61
    • 0000382638 scopus 로고
    • Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford
    • (b) Rickborn, In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 3, pp 721-732.
    • (1991) Comprehensive Organic Synthesis , vol.3 , pp. 721-732
    • Rickborn1
  • 67
    • 0036007872 scopus 로고    scopus 로고
    • and earlier reviews in this series
    • Faulkner, D. J. Nat. Prod. Rep. 2002, 19, 1-48 and earlier reviews in this series.
    • (2002) J. Nat. Prod. Rep. , vol.19 , pp. 1-48
    • Faulkner, D.1
  • 74
    • 0000717321 scopus 로고
    • and references therein
    • Krow, G. R. Tetrahedron 1981, 37, 2697-2724 and references therein.
    • (1981) Tetrahedron , vol.37 , pp. 2697-2724
    • Krow, G.R.1
  • 95
  • 96
    • 0000437994 scopus 로고
    • Paquette, L. A., Ed.; Wiley, Sons New York
    • Krow, G. R. In Organic Reactions; Paquette, L. A., Ed.; Wiley & Sons: New York, 1993; Vol. 43, pp 251-789.
    • (1993) Organic Reactions , vol.43 , pp. 251-789
    • Krow, G.R.1
  • 97
    • 0001122697 scopus 로고
    • Trost, B. M., Heathcock, C. H., Eds.; Pergamon Press: Oxford
    • (a) Colvin, E. W. In Comprehensive Organic Synthesis; Trost, B. M., Heathcock, C. H., Eds.; Pergamon Press: Oxford, 1992; Vol. 7, pp 641-651.
    • (1992) Comprehensive Organic Synthesis , vol.7 , pp. 641-651
    • Colvin, E.W.1
  • 99
    • 0141746776 scopus 로고    scopus 로고
    • note
    • This diol is a 7:1 mixture of anti and syn isomers.
  • 106
    • 0028868420 scopus 로고
    • Total synthesis of acetoxycladiell-7(16),11-dien-3-ol and cladiell-11-ene-3,6,7-triol: (a) MacMillan, D. W. C.; Overman, L. E. J. Am. Chem. Soc. 1995, 117, 10391-10392.
    • (1995) J. Am. Chem. Soc. , vol.117 , pp. 10391-10392
    • MacMillan, D.W.C.1    Overman, L.E.2
  • 108
    • 0034710488 scopus 로고    scopus 로고
    • Total synthesis of the initially proposed structure of sclerophytin A and authentic sclerophytin A: (c) Overman, L. E.; Pennington, L. D. Org. Lett. 2000, 2, 2683-2686.
    • (2000) Org. Lett. , vol.2 , pp. 2683-2686
    • Overman, L.E.1    Pennington, L.D.2
  • 123
    • 0001780886 scopus 로고    scopus 로고
    • Paquette, L. A., Ed.; Wiley & Sons: New York
    • For a comprehensive review, see: Katsuki, T.; Martin, V. S. In Organic Reactions; Paquette, L. A., Ed.; Wiley & Sons: New York, 1996; Vol. 48, pp 1-299.
    • (1996) Organic Reactions , vol.48 , pp. 1-299
    • Katsuki, T.1    Martin, V.S.2
  • 132
    • 0003533887 scopus 로고
    • Padwa, A., Ed.; Marcel Dekker: New York
    • For a review, see: Kropp, P. J. In Organic Photochemistry; Padwa, A., Ed.; Marcel Dekker: New York, 1979; Vol. 4, pp 1-142.
    • (1979) Organic Photochemistry , vol.4 , pp. 1-142
    • Kropp, P.J.1
  • 135
    • 85052771319 scopus 로고
    • Padwa, A., Ed.; Marcel Dekker: New York
    • For a review, see: (a) Childs, R. F.; Shaw, G. B. In Organic Photochemistry; Padwa, A., Ed.; Marcel Dekker: New York, 1991; Vol. 11, pp 111-225.
    • (1991) Organic Photochemistry , vol.11 , pp. 111-225
    • Childs, R.F.1    Shaw, G.B.2
  • 141
    • 85016435466 scopus 로고
    • For the synthesis of carbocyclic ring systems using pinacol-terminated cationic cyclizations developed in other laboratories, see: (a) Sano, T.; Toda, J.; Tsuda, Y. Heterocycles 1984, 22, 53-58.
    • (1984) Heterocycles , vol.22 , pp. 53-58
    • Sano, T.1    Toda, J.2    Tsuda, Y.3


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