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Volumn 65, Issue 16, 2000, Pages 4864-4870

Construction of the tricyclo[5.3.1.01,5]undecane system by a novel tandem pinacol rearrangement-ene strategy: A formal total synthesis of (±)-perhydrohistrionicotoxin

Author keywords

[No Author keywords available]

Indexed keywords

HISTRIONICOTOXIN; PERHYDROHISTRIONICOTOXIN;

EID: 0342646940     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo000136f     Document Type: Article
Times cited : (20)

References (31)
  • 2
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    • note
    • We appreciate a referee's suggestion that the second reaction of our tandem process, particularly in a case such as 2a where a five-membered ring is formed, is more properly called a Prins reaction rather than an ene reaction.
  • 4
  • 5
    • 0026596780 scopus 로고
    • and references cited
    • Chen, Y.; Lin, W. Tetrahedron Lett. 1992, 33, 1749 and references cited.
    • (1992) Tetrahedron Lett. , vol.33 , pp. 1749
    • Chen, Y.1    Lin, W.2
  • 6
    • 33947093975 scopus 로고
    • Pinacol rearrangement of a Diels-Alder derived bicyclo[2.2.2]-octene has previously been exploited in the syntheses of various natural products: (a) Monti, S. A.; Chen, S.; Yang, Y.; Yuan, S.; Bourgeois, O. P. J. Org. Chem. 1978, 43, 4062.
    • (1978) J. Org. Chem. , vol.43 , pp. 4062
    • Monti, S.A.1    Chen, S.2    Yang, Y.3    Yuan, S.4    Bourgeois, O.P.5
  • 7
    • 0011885954 scopus 로고
    • and references cited
    • (b) Monti, S. A.; Dean, T. R. J. Org. Chem. 1982, 47, 2679 and references cited.
    • (1982) J. Org. Chem. , vol.47 , pp. 2679
    • Monti, S.A.1    Dean, T.R.2
  • 12
    • 0033597912 scopus 로고    scopus 로고
    • and references cited
    • (b) For a recent synthesis of perhydrohistrionicotoxin, see; Luzzio, F. A.; Fitch, R. W. J. Org. Chem. 1999, 64, 5485 and references cited.
    • (1999) J. Org. Chem. , vol.64 , pp. 5485
    • Luzzio, F.A.1    Fitch, R.W.2
  • 13
    • 0032474797 scopus 로고    scopus 로고
    • For a good review with citations to recent work, see: Tanner, D.; Hagberg, L. Tetrahedron 1998, 54, 7907.
    • (1998) Tetrahedron , vol.54 , pp. 7907
    • Tanner, D.1    Hagberg, L.2
  • 14
    • 0342617765 scopus 로고
    • For a comprehensive review on studies before 1989, see: Kotera, M. Bull. Soc. Chim. Fr. 1989, 370.
    • (1989) Bull. Soc. Chim. Fr. , vol.370
    • Kotera, M.1
  • 20
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    • note
    • 5
  • 21
    • 0343051970 scopus 로고    scopus 로고
    • note
    • Similarly, the application of a tandem pinacol rearrangement-ene reaction to the endo alcohol 31a led to the desired six-membered tricyclic ketone 32a as the major isomer (88:12). (Matrix presentation)
  • 25
    • 0343051965 scopus 로고
    • For an example of the reduction of an alkene during a modified Wolff-Kishner reduction, see: McIntosh, J. M. Can. J. Chem. 1979, 57, 2114.
    • (1979) Can. J. Chem. , vol.57 , pp. 2114
    • McIntosh, J.M.1
  • 26
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    • Trost, B. M., Ed; Pergamon Press: New York
    • (a) Krow, G. R. Comprehensive Organic Synthesis; Trost, B. M., Ed; Pergamon Press: New York, 1991; Vol. 7, p 673.
    • (1991) Comprehensive Organic Synthesis , vol.7 , pp. 673
    • Krow, G.R.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.