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Volumn 49, Issue 18, 2008, Pages 2899-2901

On the intramolecular pyrone Diels-Alder approach to basiliolide B

Author keywords

[No Author keywords available]

Indexed keywords

BASILIOLIDE B; ISOPRENOID; PYRONE DERIVATIVE; THAPSIGARGIN; UNCLASSIFIED DRUG;

EID: 41349104635     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.03.031     Document Type: Article
Times cited : (25)

References (30)
  • 5
    • 0018942336 scopus 로고
    • For discussion and leading references, see:
    • For discussion and leading references, see:. Christensen S.B., and Ramussen U. Tetrahedron Lett. 21 (1980) 3829-3830
    • (1980) Tetrahedron Lett. , vol.21 , pp. 3829-3830
    • Christensen, S.B.1    Ramussen, U.2
  • 7
    • 41349103441 scopus 로고    scopus 로고
    • note
    • The molecular connectivity for the basiliolides was established largely through NMR spectroscopy. The absolute stereochemistry is unknown.
  • 11
    • 41349098567 scopus 로고    scopus 로고
    • note
    • The stereogenic centers are at adjoining carbons. The contiguous nature of the stereocenters simplifies rather than confounds the problem.
  • 12
    • 41349114226 scopus 로고    scopus 로고
    • Portions of this work have been presented: (a) Kozytska, M. V.; Dudley, G. B. Abstracts of Papers 58th Southeast Regional Meeting of the American Chemical Society, Augusta, GA, November 1-4, 2006; American Chemical Society; Washington, DC, 2006; SRM06 011.
    • Portions of this work have been presented: (a) Kozytska, M. V.; Dudley, G. B. Abstracts of Papers 58th Southeast Regional Meeting of the American Chemical Society, Augusta, GA, November 1-4, 2006; American Chemical Society; Washington, DC, 2006; SRM06 011.
  • 13
    • 41349092299 scopus 로고    scopus 로고
    • Kozytska, M. V.; Dudley, G. B. Abstracts of Papers 234th National Meeting of the American Chemical Society, Boston, MA, August 19-23, 2007; American Chemical Society; Washington, DC, 2007; ORGN 1012.
    • Kozytska, M. V.; Dudley, G. B. Abstracts of Papers 234th National Meeting of the American Chemical Society, Boston, MA, August 19-23, 2007; American Chemical Society; Washington, DC, 2007; ORGN 1012.
  • 14
    • 0027054952 scopus 로고
    • Relevant applications of 5-halo-2-pyrones in Diels-Alder reactions:
    • Relevant applications of 5-halo-2-pyrones in Diels-Alder reactions:. Afarinkia K., and Posner G.H. Tetrahedron Lett. 33 (1992) 7839-7842
    • (1992) Tetrahedron Lett. , vol.33 , pp. 7839-7842
    • Afarinkia, K.1    Posner, G.H.2
  • 21
    • 41349083785 scopus 로고    scopus 로고
    • note
    • Although their report does not specifically address IMPDA reactions of 5-halo-2-pyrones, Nelson and Stoltz also highlighted their potential utility for the synthesis of basiliolide B (Ref. 13).
  • 22
    • 41349102558 scopus 로고    scopus 로고
    • See Supplementary data for experimental procedures and data.
    • See Supplementary data for experimental procedures and data.
  • 29
    • 41349083565 scopus 로고    scopus 로고
    • note
    • We elected to examine a three-carbon tethered substrate (13) rather than build Thorpe-Ingold assistance into a four-carbon tether.


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