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Volumn 37, Issue 3, 1996, Pages 371-374

Total synthesis of (+)-goniodiol

Author keywords

[No Author keywords available]

Indexed keywords

CYTOTOXIC AGENT; GONIODIOL; LACTONE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0030059280     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(95)02125-6     Document Type: Article
Times cited : (33)

References (29)
  • 1
    • 0029047088 scopus 로고
    • and references cited therein
    • For the structure and syntheses of other styryl lactones see : Shing, T.K.M. ; Tsui, H.C. ; Zhou, Z.H. J. Org. Chem. 1995, 60, 3121-3130 and references cited therein.
    • (1995) J. Org. Chem. , vol.60 , pp. 3121-3130
    • Shing, T.K.M.1    Tsui, H.C.2    Zhou, Z.H.3
  • 12
    • 33744863869 scopus 로고
    • (c) for a review on the diastereoselective reduction of α-hydroxy or alkoxy ketones see : Oishi, T. ; Nakata, T. Acc. Chem. Res. 1994, 17, 338-344.
    • (1994) Acc. Chem. Res. , vol.17 , pp. 338-344
    • Oishi, T.1    Nakata, T.2
  • 13
    • 33845556313 scopus 로고
    • (a) The anti-product can be stereoselectively obtained by reduction with Vitride®, at -78°C, of the O-BOM protected α-ketol 4 (ratio = 4:1)
    • (a) The anti-product can be stereoselectively obtained by reduction with Vitride®, at -78°C, of the O-BOM protected α-ketol 4 (ratio = 4:1) ; (b) Gemal, A.L. ; Luche, J.L. J. Am. Chem. Soc. 1981, 103, 5454-5459.
    • (1981) J. Am. Chem. Soc. , vol.103 , pp. 5454-5459
    • Gemal, A.L.1    Luche, J.L.2
  • 17
    • 85031228481 scopus 로고    scopus 로고
    • note
    • Analytical and spectral data were obtained for all new compounds and are consistent with the structure assigned.
  • 21
    • 0000894454 scopus 로고
    • Cha, J.K. ; Christ, W.J. ; Kishi, Y. Tetrahedron Lett. 1983, 24, 3943-3946 ; Cha, J.K. ; Christ, W.J. ; Kishi, Y. Tetrahedron 1984, 40, 2247-2255.
    • (1983) Tetrahedron Lett. , vol.24 , pp. 3943-3946
    • Cha, J.K.1    Christ, W.J.2    Kishi, Y.3
  • 22
    • 33748632563 scopus 로고
    • Cha, J.K. ; Christ, W.J. ; Kishi, Y. Tetrahedron Lett. 1983, 24, 3943-3946 ; Cha, J.K. ; Christ, W.J. ; Kishi, Y. Tetrahedron 1984, 40, 2247-2255.
    • (1984) Tetrahedron , vol.40 , pp. 2247-2255
    • Cha, J.K.1    Christ, W.J.2    Kishi, Y.3
  • 26
    • 0000888642 scopus 로고
    • For a recent example of TBDPS migrations see : Marshall, J.A. ; Tang, Y. J. Org. Chem. 1994, 59, 1457-1464. For mechanistic aspects of 1,2-0-trialkylsilyl group transfer see : Jones, S.S. ; Reese, C.B. J. Chem. Soc. Perkin Trans. I 1979, 2762-2764.
    • (1994) J. Org. Chem. , vol.59 , pp. 1457-1464
    • Marshall, J.A.1    Tang, Y.2
  • 27
    • 37049108985 scopus 로고
    • For a recent example of TBDPS migrations see : Marshall, J.A. ; Tang, Y. J. Org. Chem. 1994, 59, 1457-1464. For mechanistic aspects of 1,2-0-trialkylsilyl group transfer see : Jones, S.S. ; Reese, C.B. J. Chem. Soc. Perkin Trans. I 1979, 2762-2764.
    • (1979) J. Chem. Soc. Perkin Trans. I , pp. 2762-2764
    • Jones, S.S.1    Reese, C.B.2
  • 28
    • 85031229941 scopus 로고    scopus 로고
    • note
    • A diastereomer of the epoxide 2 has been used in the synthesis of another styryl lactone : (±)-9-deoxy goniopypyrone see ref. 8.
  • 29
    • 85031214246 scopus 로고    scopus 로고
    • note
    • 2O greatly enhanced the reaction rate and improved the yield (private communication).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.