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Volumn 5, Issue 22, 2003, Pages 4223-4226

Synthetic Studies toward FR182877. Remarkable Solvent Effect in the Vinylogous Morita-Baylis-Hillman Cyclization

Author keywords

[No Author keywords available]

Indexed keywords

ANTIMITOTIC AGENT; FR 182877; SOLVENT; UNCLASSIFIED DRUG;

EID: 0344944868     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0357550     Document Type: Article
Times cited : (71)

References (38)
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    • Trost, B. M., Fleming, I., Paquette, L. A., Eds.; Pergamon: Oxford
    • Roush, W. R. Intramolecular Diels-Alder Reactions. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Paquette, L. A., Eds.; Pergamon: Oxford, 1991; Vol. 5, p 513.
    • (1991) Comprehensive Organic Synthesis , vol.5 , pp. 513
    • Roush, W.R.1
  • 21
    • 0345681827 scopus 로고    scopus 로고
    • For recent studies, see: (a) Grainger, R. S.; Leadbeater, N. E.; Pamies, A. M. Catal. Commun. 2002, 3, 449. (b) Shi, M.; Xu, Y.-M.; Zhao, G.-L.; Wu, X.-F. Eur. J. Org. Chem. 2002, 3666. (c) Hayashi, Y.; Okado, K.; Ashimine, I.; Shoji, M. Tetrahedron Lett. 2002, 43, 8683.
    • (2002) Catal. Commun. , vol.3 , pp. 449
    • Grainger, R.S.1    Leadbeater, N.E.2    Pamies, A.M.3
  • 22
    • 0036846203 scopus 로고    scopus 로고
    • For recent studies, see: (a) Grainger, R. S.; Leadbeater, N. E.; Pamies, A. M. Catal. Commun. 2002, 3, 449. (b) Shi, M.; Xu, Y.-M.; Zhao, G.-L.; Wu, X.-F. Eur. J. Org. Chem. 2002, 3666. (c) Hayashi, Y.; Okado, K.; Ashimine, I.; Shoji, M. Tetrahedron Lett. 2002, 43, 8683.
    • (2002) Eur. J. Org. Chem. , pp. 3666
    • Shi, M.1    Xu, Y.-M.2    Zhao, G.-L.3    Wu, X.-F.4
  • 23
    • 0037175462 scopus 로고    scopus 로고
    • For recent studies, see: (a) Grainger, R. S.; Leadbeater, N. E.; Pamies, A. M. Catal. Commun. 2002, 3, 449. (b) Shi, M.; Xu, Y.-M.; Zhao, G.-L.; Wu, X.-F. Eur. J. Org. Chem. 2002, 3666. (c) Hayashi, Y.; Okado, K.; Ashimine, I.; Shoji, M. Tetrahedron Lett. 2002, 43, 8683.
    • (2002) Tetrahedron Lett. , vol.43 , pp. 8683
    • Hayashi, Y.1    Okado, K.2    Ashimine, I.3    Shoji, M.4
  • 33
    • 0001260024 scopus 로고    scopus 로고
    • A puzzling shift in reaction diastereoselectivity was observed by Yang and Chen in an intermolecular Baylis-Hillman catalyzed by DABCO in THF/water versus DMSO: Yang, K.-S.; Chen, K. Org. Lett. 2000, 2, 729.
    • (2000) Org. Lett. , vol.2 , pp. 729
    • Yang, K.-S.1    Chen, K.2
  • 34
    • 0345555684 scopus 로고    scopus 로고
    • note
    • Molecular modeling using Spartan (Monte Carlo search with MMF94) estimates a 5 kcal/mol preference for the (E)-olefin geometry as shown with 11.
  • 37
    • 0345124173 scopus 로고    scopus 로고
    • note
    • Our synthesis of 13 will be reported elsewhere.
  • 38
    • 0345555685 scopus 로고    scopus 로고
    • note
    • Tricycles 7, 14, and 15 are readily oxidized in the presence of air; see Supporting Information.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.