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Volumn , Issue 7, 2000, Pages 1020-1026

Synthesis of the first 'inside-outside' eight-membered ring via ringclosing metathesis: A total synthesis of (+/-)-asteriscanolide

Author keywords

Metathesis; Pauson Khand cycloaddition; Ring closing; Total synthesis; Transition metal mediated reactions

Indexed keywords

ASTERISCANOLIDE; SESQUITERPENE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0033938566     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2000-6302     Document Type: Article
Times cited : (42)

References (41)
  • 7
    • 0001647405 scopus 로고
    • Miller, S. J.; Kim, S. H.; Chen, Z. R.; Grubbs, R. H. J. Am. Chem. Soc. 1995, 117, 2108. Schuster, S; Blechert, S. Angew. Chem., Int. Ed. Engl. 1997, 36, 2036. Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413. Alkene Metathesis in Organic Synthesis. In Topics in Organometallic Chemistry, Vol. 1; Furstner, A., Ed.; Springer-Verlag: Berlin, 1998.
    • (1995) J. Am. Chem. Soc. , vol.117 , pp. 2108
    • Miller, S.J.1    Kim, S.H.2    Chen, Z.R.3    Grubbs, R.H.4
  • 8
    • 0030771019 scopus 로고    scopus 로고
    • Miller, S. J.; Kim, S. H.; Chen, Z. R.; Grubbs, R. H. J. Am. Chem. Soc. 1995, 117, 2108. Schuster, S; Blechert, S. Angew. Chem., Int. Ed. Engl. 1997, 36, 2036. Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413. Alkene Metathesis in Organic Synthesis. In Topics in Organometallic Chemistry, Vol. 1; Furstner, A., Ed.; Springer-Verlag: Berlin, 1998.
    • (1997) Angew. Chem., Int. Ed. Engl. , vol.36 , pp. 2036
    • Schuster, S.1    Blechert, S.2
  • 9
    • 0032580376 scopus 로고    scopus 로고
    • Miller, S. J.; Kim, S. H.; Chen, Z. R.; Grubbs, R. H. J. Am. Chem. Soc. 1995, 117, 2108. Schuster, S; Blechert, S. Angew. Chem., Int. Ed. Engl. 1997, 36, 2036. Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413. Alkene Metathesis in Organic Synthesis. In Topics in Organometallic Chemistry, Vol. 1; Furstner, A., Ed.; Springer-Verlag: Berlin, 1998.
    • (1998) Tetrahedron , vol.54 , pp. 4413
    • Grubbs, R.H.1    Chang, S.2
  • 10
    • 0002673788 scopus 로고    scopus 로고
    • Alkene metathesis in organic synthesis
    • Springer-Verlag: Berlin
    • Miller, S. J.; Kim, S. H.; Chen, Z. R.; Grubbs, R. H. J. Am. Chem. Soc. 1995, 117, 2108. Schuster, S; Blechert, S. Angew. Chem., Int. Ed. Engl. 1997, 36, 2036. Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413. Alkene Metathesis in Organic Synthesis. In Topics in Organometallic Chemistry, Vol. 1; Furstner, A., Ed.; Springer-Verlag: Berlin, 1998.
    • (1998) Topics in Organometallic Chemistry , vol.1
    • Furstner, A.1
  • 11
    • 8544248595 scopus 로고    scopus 로고
    • For reviews, see: Kim, S.; Winkler, J. D. Chem. Soc. Rev. 1997, 26, 387. Rigby, J. H. In Studies in Natural Products Chemistry, Vol. 12 (part H); Rahman, A. -U., Ed.; Elsevier: Amsterdam, 1993; p 233.
    • (1997) Chem. Soc. Rev. , vol.26 , pp. 387
    • Kim, S.1    Winkler, J.D.2
  • 12
    • 0006957213 scopus 로고
    • Elsevier: Amsterdam
    • For reviews, see: Kim, S.; Winkler, J. D. Chem. Soc. Rev. 1997, 26, 387. Rigby, J. H. In Studies in Natural Products Chemistry, Vol. 12 (part H); Rahman, A. -U., Ed.; Elsevier: Amsterdam, 1993; p 233.
    • (1993) Studies in Natural Products Chemistry , vol.12 , Issue.PART H , pp. 233
    • Rigby, J.H.1    Rahman, A.-U.2
  • 14
    • 0032537201 scopus 로고    scopus 로고
    • Rigby, J. H.; Claire, V. S.; Cuisiat, S. V.; Heeg, M. J. J. Org. Chem. 1996, 61, 7992 Rigby, J. H.; Hu, J; Heeg, M. J. Tetrahedron Lett. 1998, 39, 2265.
    • (1998) Tetrahedron Lett. , vol.39 , pp. 2265
    • Rigby, J.H.1    Hu, J.2    Heeg, M.J.3
  • 16
  • 19
    • 0001647405 scopus 로고
    • Miller, S. J.; Kim, S. H.; Chen, Z. R.; Grubbs, R. H. J. Am. Chem. Soc. 1995, 117, 2108. Schuster, S; Blechert, S. Angew. Chem., Int. Ed. Engl. 1997, 36, 2036. Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413. Alkene Metathesis in Organic Synthesis. In Topics in Organometallic Chemistry, Vol. 1; Furstner, A., Ed.; Springer-Verlag: Berlin, 1998.
    • (1995) J. Am. Chem. Soc. , vol.117 , pp. 2108
    • Miller, S.J.1    Kim, S.H.2    Chen, Z.R.3    Grubbs, R.H.4
  • 20
    • 0030771019 scopus 로고    scopus 로고
    • Miller, S. J.; Kim, S. H.; Chen, Z. R.; Grubbs, R. H. J. Am. Chem. Soc. 1995, 117, 2108. Schuster, S; Blechert, S. Angew. Chem., Int. Ed. Engl. 1997, 36, 2036. Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413. Alkene Metathesis in Organic Synthesis. In Topics in Organometallic Chemistry, Vol. 1; Furstner, A., Ed.; Springer-Verlag: Berlin, 1998.
    • (1997) Angew. Chem., Int. Ed. Engl. , vol.36 , pp. 2036
    • Schuster, S.1    Blechert, S.2
  • 21
    • 0032580376 scopus 로고    scopus 로고
    • Miller, S. J.; Kim, S. H.; Chen, Z. R.; Grubbs, R. H. J. Am. Chem. Soc. 1995, 117, 2108. Schuster, S; Blechert, S. Angew. Chem., Int. Ed. Engl. 1997, 36, 2036. Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413. Alkene Metathesis in Organic Synthesis. In Topics in Organometallic Chemistry, Vol. 1; Furstner, A., Ed.; Springer-Verlag: Berlin, 1998.
    • (1998) Tetrahedron , vol.54 , pp. 4413
    • Grubbs, R.H.1    Chang, S.2
  • 22
    • 0002673788 scopus 로고    scopus 로고
    • Alkene metathesis in organic synthesis
    • Springer-Verlag: Berlin
    • Miller, S. J.; Kim, S. H.; Chen, Z. R.; Grubbs, R. H. J. Am. Chem. Soc. 1995, 117, 2108. Schuster, S; Blechert, S. Angew. Chem., Int. Ed. Engl. 1997, 36, 2036. Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413. Alkene Metathesis in Organic Synthesis. In Topics in Organometallic Chemistry, Vol. 1; Furstner, A., Ed.; Springer-Verlag: Berlin, 1998.
    • (1998) Topics in Organometallic Chemistry , vol.1
    • Furstner, A.1
  • 23
    • 0001334715 scopus 로고
    • Trost, B. M., Ed.; Pergamon: Oxford
    • Schore, N. E. In Comprehensive Organic Synthesis, Vol. 5; Trost, B. M., Ed.; Pergamon: Oxford, 1991; p 1037. Schore, N. E. Org. Reactions 1991, 40, 1. Schore, N. E. In Comprehensive Organometallic Chemistry-II, Vol. 12; Hegedus, L. S., Ed.; Pergamon: Oxford, 1995; p 703. Geis, O.; Schmalz, H. -G. Angew. Chem., Int. Ed. Engl. 1998, 37, 911.
    • (1991) Comprehensive Organic Synthesis , vol.5 , pp. 1037
    • Schore, N.E.1
  • 24
    • 0002307453 scopus 로고
    • Schore, N. E. In Comprehensive Organic Synthesis, Vol. 5; Trost, B. M., Ed.; Pergamon: Oxford, 1991; p 1037. Schore, N. E. Org. Reactions 1991, 40, 1. Schore, N. E. In Comprehensive Organometallic Chemistry-II, Vol. 12; Hegedus, L. S., Ed.; Pergamon: Oxford, 1995; p 703. Geis, O.; Schmalz, H. -G. Angew. Chem., Int. Ed. Engl. 1998, 37, 911.
    • (1991) Org. Reactions , vol.40 , pp. 1
    • Schore, N.E.1
  • 25
    • 0001136410 scopus 로고
    • Hegedus, L. S., Ed.; Pergamon: Oxford
    • Schore, N. E. In Comprehensive Organic Synthesis, Vol. 5; Trost, B. M., Ed.; Pergamon: Oxford, 1991; p 1037. Schore, N. E. Org. Reactions 1991, 40, 1. Schore, N. E. In Comprehensive Organometallic Chemistry-II, Vol. 12; Hegedus, L. S., Ed.; Pergamon: Oxford, 1995; p 703. Geis, O.; Schmalz, H. -G. Angew. Chem., Int. Ed. Engl. 1998, 37, 911.
    • (1995) Comprehensive Organometallic Chemistry-II , vol.12 , pp. 703
    • Schore, N.E.1
  • 26
    • 0031971911 scopus 로고    scopus 로고
    • Schore, N. E. In Comprehensive Organic Synthesis, Vol. 5; Trost, B. M., Ed.; Pergamon: Oxford, 1991; p 1037. Schore, N. E. Org. Reactions 1991, 40, 1. Schore, N. E. In Comprehensive Organometallic Chemistry-II, Vol. 12; Hegedus, L. S., Ed.; Pergamon: Oxford, 1995; p 703. Geis, O.; Schmalz, H. -G. Angew. Chem., Int. Ed. Engl. 1998, 37, 911.
    • (1998) Angew. Chem., Int. Ed. Engl. , vol.37 , pp. 911
    • Geis, O.1    Schmalz, H.-G.2
  • 29
    • 0001383865 scopus 로고
    • Krafft, M. E. J. Am. Chem. Soc. 1988, 110, 968. Krafft, M. E.; Juliano, C. A. J. Org. Chem. 1992, 57, 5106. Krafft, M. E.; Juliano, C. A.; Scott, I. L.; Wright, C.; McEachin, M. D. J. Am. Chem. Soc. 1991, 113, 1693.
    • (1988) J. Am. Chem. Soc. , vol.110 , pp. 968
    • Krafft, M.E.1
  • 30
    • 0000925820 scopus 로고
    • Krafft, M. E. J. Am. Chem. Soc. 1988, 110, 968. Krafft, M. E.; Juliano, C. A. J. Org. Chem. 1992, 57, 5106. Krafft, M. E.; Juliano, C. A.; Scott, I. L.; Wright, C.; McEachin, M. D. J. Am. Chem. Soc. 1991, 113, 1693.
    • (1992) J. Org. Chem. , vol.57 , pp. 5106
    • Krafft, M.E.1    Juliano, C.A.2
  • 35
    • 0000751968 scopus 로고
    • Keck, G. E.; Savin, K. A.; Cressman, E. N. K.; Abbott, D. E. J. Org. Chem. 1994, 59, 7889. Keck, G. E.; Abbott, D. E. Tetrahedron Lett. 1984, 25, 1883.
    • (1984) Tetrahedron Lett. , vol.25 , pp. 1883
    • Keck, G.E.1    Abbott, D.E.2
  • 38
    • 0342473123 scopus 로고    scopus 로고
    • unpublished results. matrix presented
    • We have also synthesized the following inside-outside compounds 20-22. Krafft M. E.; Cheung, Y. Y. unpublished results. (matrix presented)
    • Krafft, M.E.1    Cheung, Y.Y.2
  • 40
    • 0343342591 scopus 로고    scopus 로고
    • note
    • Structure minimizations were carried out using Molecular Mechanics available in the CAChe system (Oxford Molecular Group) Version 4.0.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.