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Volumn 121, Issue 32, 1999, Pages 7423-7424

Total synthesis of (-)-cylindrocyclophane F [10]

Author keywords

[No Author keywords available]

Indexed keywords

CYLINDROCYCLOPHANE F; NATURAL PRODUCT; UNCLASSIFIED DRUG;

EID: 0033581176     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja991538b     Document Type: Letter
Times cited : (51)

References (34)
  • 4
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    • For the preparation of related [7, 7]-paracyclophanes, see: (a) Schubert, W. B.; Sweeney, W. A.; Latourette, H. K. J. Am. Chem. Soc. 1954, 76, 5462. (b) Staab, H. A.; Matzke, G.; Frieger, C. Chem. Ber. 1987, 120, 89. (c) Mascal, M.; Kerdelhue, J.-L.; Batsanov, A. S.; Begley, M. J. J. Chem. Soc., Perkin Trans. 1 1996, 1141.
    • (1954) J. Am. Chem. Soc. , vol.76 , pp. 5462
    • Schubert, W.B.1    Sweeney, W.A.2    Latourette, H.K.3
  • 5
    • 0003587608 scopus 로고
    • For the preparation of related [7, 7]-paracyclophanes, see: (a) Schubert, W. B.; Sweeney, W. A.; Latourette, H. K. J. Am. Chem. Soc. 1954, 76, 5462. (b) Staab, H. A.; Matzke, G.; Frieger, C. Chem. Ber. 1987, 120, 89. (c) Mascal, M.; Kerdelhue, J.-L.; Batsanov, A. S.; Begley, M. J. J. Chem. Soc., Perkin Trans. 1 1996, 1141.
    • (1987) Chem. Ber. , vol.120 , pp. 89
    • Staab, H.A.1    Matzke, G.2    Frieger, C.3
  • 6
    • 0344070380 scopus 로고    scopus 로고
    • For the preparation of related [7, 7]-paracyclophanes, see: (a) Schubert, W. B.; Sweeney, W. A.; Latourette, H. K. J. Am. Chem. Soc. 1954, 76, 5462. (b) Staab, H. A.; Matzke, G.; Frieger, C. Chem. Ber. 1987, 120, 89. (c) Mascal, M.; Kerdelhue, J.-L.; Batsanov, A. S.; Begley, M. J. J. Chem. Soc., Perkin Trans. 1 1996, 1141.
    • (1996) J. Chem. Soc., Perkin Trans. 1 , pp. 1141
    • Mascal, M.1    Kerdelhue, J.-L.2    Batsanov, A.S.3    Begley, M.J.4
  • 10
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    • Ph.D. Dissertation, University of Pennsylvania
    • To date all attempts to prepare the macrocycle in one step by a variety of dimerization processes have been unsuccessful. Paone, D. V. Ph.D. Dissertation, University of Pennsylvania, 1998.
    • (1998)
    • Paone, D.V.1
  • 12
    • 0032580376 scopus 로고    scopus 로고
    • For recent reviews, see: (a) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413. (b) Armstrong, S. K. J. Chem. Soc., Perkin Trans. 1 1998, 371. (c) Schuster, M.; Blechert, S. Angew. Chem., Int. Ed. Engl. 1997, 36, 2037. (d) Grubbs, R. H.; Miller, S. J.; Fu, G. C. Acc. Chem. Res. 1995, 28, 446.
    • (1998) Tetrahedron , vol.54 , pp. 4413
    • Grubbs, R.H.1    Chang, S.2
  • 13
    • 28244440935 scopus 로고    scopus 로고
    • For recent reviews, see: (a) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413. (b) Armstrong, S. K. J. Chem. Soc., Perkin Trans. 1 1998, 371. (c) Schuster, M.; Blechert, S. Angew. Chem., Int. Ed. Engl. 1997, 36, 2037. (d) Grubbs, R. H.; Miller, S. J.; Fu, G. C. Acc. Chem. Res. 1995, 28, 446.
    • (1998) J. Chem. Soc., Perkin Trans. 1 , pp. 371
    • Armstrong, S.K.1
  • 14
    • 0000755941 scopus 로고    scopus 로고
    • For recent reviews, see: (a) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413. (b) Armstrong, S. K. J. Chem. Soc., Perkin Trans. 1 1998, 371. (c) Schuster, M.; Blechert, S. Angew. Chem., Int. Ed. Engl. 1997, 36, 2037. (d) Grubbs, R. H.; Miller, S. J.; Fu, G. C. Acc. Chem. Res. 1995, 28, 446.
    • (1997) Angew. Chem., Int. Ed. Engl. , vol.36 , pp. 2037
    • Schuster, M.1    Blechert, S.2
  • 15
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    • For recent reviews, see: (a) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413. (b) Armstrong, S. K. J. Chem. Soc., Perkin Trans. 1 1998, 371. (c) Schuster, M.; Blechert, S. Angew. Chem., Int. Ed. Engl. 1997, 36, 2037. (d) Grubbs, R. H.; Miller, S. J.; Fu, G. C. Acc. Chem. Res. 1995, 28, 446.
    • (1995) Acc. Chem. Res. , vol.28 , pp. 446
    • Grubbs, R.H.1    Miller, S.J.2    Fu, G.C.3
  • 24
    • 0032367925 scopus 로고    scopus 로고
    • For a review of ynolate anions, see: Shido, M. Chem. Soc. Rev. 1998, 27, 367.
    • (1998) Chem. Soc. Rev. , vol.27 , pp. 367
    • Shido, M.1
  • 26
    • 0344573845 scopus 로고    scopus 로고
    • note
    • Imide (+)-10 was prepared in 97% yield from (1S,2R)-(+)-norephedrine derived oxazolidinone and hexanoyl chloride (n-BuLi, THF, -78 °C).
  • 28
    • 0344573844 scopus 로고    scopus 로고
    • note
    • 13C NMR, and high-resolution mass spectra.
  • 29
    • 0344573841 scopus 로고    scopus 로고
    • Ph.D. Dissertation, University of Pennsylvania
    • The integrity of the chiral center in (-)-5 was established rigorously. Paone, D. V. Ph.D. Dissertation, University of Pennsylvania, 1998.
    • (1998)
    • Paone, D.V.1
  • 32
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    • University of Pennsylvania, unpublished results
    • Carroll, P. J. University of Pennsylvania, unpublished results.
    • Carroll, P.J.1
  • 34
    • 0344573843 scopus 로고    scopus 로고
    • note
    • We thank Professor Moore (University of Hawaii) for a generous sample of authentic (-)-cylindrocyclophane F.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.