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Volumn 6, Issue 8, 2004, Pages 1317-1319

Rapid assembly of the bicyclo[5.3.1]undecenone core of Penostatin F: A successive Diels-Alder/Claisen reaction strategy with an efficient stereochemical relay

Author keywords

[No Author keywords available]

Indexed keywords

2 DECENAL; ACETOACETIC ACID; BICYCLO COMPOUND; BICYCLO[5.3.1]UNDECENONE; CHEMICAL COMPOUND; METHYLACETOACETATE; PENOSTATIN F; UNCLASSIFIED DRUG;

EID: 2542476902     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol049680r     Document Type: Article
Times cited : (24)

References (23)
  • 4
    • 0002502917 scopus 로고
    • For a review that summarizes different approaches for the synthesis of bicyclo[5.3.1]undecene of taxol, see: Boa, A. N.; Jenkins, P. R.; Lawrence, N. J. Contemp. Org. Synth. 1994, 1, 47-75. (c) Sheehan, S. M.; Lalic, G.; Chen, J. S.; Shair, M. D. Angew. Chem., Int. Ed. 2000, 39, 2714.
    • (1994) Contemp. Org. Synth. , vol.1 , pp. 47-75
    • Boa, A.N.1    Jenkins, P.R.2    Lawrence, N.J.3
  • 5
    • 0034604574 scopus 로고    scopus 로고
    • For a review that summarizes different approaches for the synthesis of bicyclo[5.3.1]undecene of taxol, see: Boa, A. N.; Jenkins, P. R.; Lawrence, N. J. Contemp. Org. Synth. 1994, 1, 47-75. (c) Sheehan, S. M.; Lalic, G.; Chen, J. S.; Shair, M. D. Angew. Chem., Int. Ed. 2000, 39, 2714.
    • (2000) Angew. Chem., Int. Ed. , vol.39 , pp. 2714
    • Sheehan, S.M.1    Lalic, G.2    Chen, J.S.3    Shair, M.D.4
  • 8
    • 0032510338 scopus 로고    scopus 로고
    • and references therein
    • (a) For review on tether in cycloaddition, see: Shea, K. J.; Zandi, K. S.; Gauthier, D. R. Tetrahedron 1998, 54, 2289 and references therein.
    • (1998) Tetrahedron , vol.54 , pp. 2289
    • Shea, K.J.1    Zandi, K.S.2    Gauthier, D.R.3
  • 21
    • 2542464585 scopus 로고    scopus 로고
    • note
    • No cycloadducts were isolated when using method A (entries 1-3). A complete degradation of dienes 4a and 4b was observed.
  • 22
    • 2542463637 scopus 로고    scopus 로고
    • note
    • 1H NMR COSY and NOESY experiments.
  • 23
    • 2542430797 scopus 로고    scopus 로고
    • note
    • All attempts to perform this sequence in tandem resulted in the degradation of the Diels-Alder adduct.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.