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Volumn 75, Issue 11, 2010, Pages 3871-3874

Catalytic enantioselective total synthesis of (-)-platyphyllide and its structural revision

Author keywords

[No Author keywords available]

Indexed keywords

ABSOLUTE CONFIGURATION; ASYMMETRIC TOTAL SYNTHESIS; CYCLOHEXENES; DIELS-ALDER ADDUCT; DIELS-ALDER REACTION; ELECTRON-DEFICIENT; ENANTIOSELECTIVE TOTAL SYNTHESIS; NATURAL COMPOUNDS;

EID: 77952962171     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo1003746     Document Type: Article
Times cited : (26)

References (39)
  • 10
    • 0027321820 scopus 로고
    • For examples of natural product syntheses or synthetic studies without elimination of the alkoxy group of Danishefsky-type diene, see
    • For examples of natural product syntheses or synthetic studies without elimination of the alkoxy group of Danishefsky-type diene, see: Yamamoto, N.; Isobe, M. Tetrahedron 1993, 49, 6581
    • (1993) Tetrahedron , vol.49 , pp. 6581
    • Yamamoto, N.1    Isobe, M.2
  • 25
    • 0000085579 scopus 로고
    • Successful examples of Ito-Saegusa or other oxidations with a β-ethereal group have been limited to hydropyran- or hydrofuran-type compounds; see
    • Successful examples of Ito-Saegusa or other oxidations with a β-ethereal group have been limited to hydropyran- or hydrofuran-type compounds; see: Danishefsky, S. J.; Pearson, W. H. J. Org. Chem. 1983, 48, 3865
    • (1983) J. Org. Chem. , vol.48 , pp. 3865
    • Danishefsky, S.J.1    Pearson, W.H.2
  • 30
    • 37049092382 scopus 로고
    • note
    • This versatile building block has been constructed by the Diels-Alder reaction of 1,1-dimethoxy-3-siloxy-1,3-butadiene or its derivatives with alkenes. The Diels-Alder reaction of such dienes with alkyne or quinone was also a very powerful method for synthesizing resorcinols. However, they require several steps for preparation. For preparation, see
    • (1976) J. Chem. Soc. Perkin Trans. 1 , vol.43 , pp. 1852
    • Banville, J.1    Brassard, P.2    Danishefsky, S.3    Singh, R.K.4    Gammill, R.B.5
  • 31
    • 37049092382 scopus 로고
    • For various conversions of the Diels-Alder adduct derived from the diene
    • Banville, J.; Brassard, P. J. Chem. Soc. Perkin Trans. 1 1976, 1852 For various conversions of the Diels-Alder adduct derived from the diene, see
    • (1976) J. Chem. Soc. Perkin Trans. 1 , pp. 1852
    • Banville, J.1    Brassard, P.2
  • 32
    • 0001098723 scopus 로고
    • Danishefsky S., Singh R. K., Gammill R. B.
    • (1978) J. Org. Chem. , vol.43 , pp. 379
  • 34
    • 77952992684 scopus 로고    scopus 로고
    • note
    • The isomerized product 18 was obtained in 22% yield (containing trace inseparable compound) at this step. So far, we do not have any information about the mechanism of this isomerization. Further screenings of the conditions to selectively give 18 and a mechanistic study are in progress.
  • 37
    • 77953004744 scopus 로고    scopus 로고
    • note
    • We have previously determined the absolute configuration of Diels-Alder adducts of our asymmetric reaction using (S)-BINAMIDE by conversion to a known compound. (3a) For details, see the Supporting Information.
  • 38
    • 77952970845 scopus 로고    scopus 로고
    • note
    • The absolute configuration of synthetic (+)-platyphyllide was also estimated by Moshers method. For details, see the Supporting Information.
  • 39
    • 77953007044 scopus 로고    scopus 로고
    • note
    • CCDC 773055 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.