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Volumn 34, Issue 6, 2004, Pages 961-983

A Novel Synthetic Approach from Diosgenin to a 17α-Hydroxy Orthoester via a Regio- and Stereo-Specific Rearrangement of an Epoxy Ester

Author keywords

Cholesterol; Diosgenin; Epoxy ester; Orthoester; Regio specific and stereo specific rearrangement

Indexed keywords

17ALPHA HYDROXY ORTHOESTER; CHOLESTEROL; DIOSGENIN; EPOXIDE; ESTER; UNCLASSIFIED DRUG;

EID: 1842585946     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1081/SCC-120028627     Document Type: Article
Times cited : (12)

References (14)
  • 2
    • 0026031093 scopus 로고
    • New antiviral sterol disulfate ortho esters from the marine sponge Petrosia weinbergi
    • Koehn, F.E.; Gunasekera, M.; Cross, S.S. New antiviral sterol disulfate ortho esters from the marine sponge Petrosia weinbergi. J. Org. Chem. 1991, 56, 1322-1325.
    • (1991) J. Org. Chem. , vol.56 , pp. 1322-1325
    • Koehn, F.E.1    Gunasekera, M.2    Cross, S.S.3
  • 3
    • 20244385388 scopus 로고
    • Sterol disulfates and methods of use
    • US Patent 5,079,239, January 7, 1992
    • Sun, H.H.; Cross, S.S.; Koehn, F.E.; Gunasekera, M. Sterol disulfates and methods of use. US Patent 5,079,239, January 7, 1992, Chem. Abstr. 1992, 116, 207800.
    • (1992) Chem. Abstr. , vol.116 , pp. 207800
    • Sun, H.H.1    Cross, S.S.2    Koehn, F.E.3    Gunasekera, M.4
  • 4
    • 0037134177 scopus 로고    scopus 로고
    • A biomimetic approach to the synthesis of an antiviral marine steroidal orthoester
    • Giner, J.-L.; Faraldos, J.A. A biomimetic approach to the synthesis of an antiviral marine steroidal orthoester. J. Org. Chem. 2002, 67, 2717-2720.
    • (2002) J. Org. Chem. , vol.67 , pp. 2717-2720
    • Giner, J.-L.1    Faraldos, J.A.2
  • 5
    • 0037067334 scopus 로고    scopus 로고
    • Synthesis of 2-methyl-D-erythriol via epoxy-orthoester rearrangement
    • Giner, J.-L.; Ferris, W.V., Jr.; Mullins, J.J. Synthesis of 2-methyl-D-erythriol via epoxy-orthoester rearrangement. J. Org. Chem. 2002, 67, 4856-4859.
    • (2002) J. Org. Chem. , vol.67 , pp. 4856-4859
    • Giner, J.-L.1    Ferris Jr., W.V.2    Mullins, J.J.3
  • 6
    • 0001678648 scopus 로고
    • Acylated cholestane glycosides from the bulbs of Ornithogalum saundersiae
    • (a) Kubo, S.; Mimaki, Y.; Terao, M.; Sashida, Y.; Nikaido, T.; Ohmoto, T. Acylated cholestane glycosides from the bulbs of Ornithogalum saundersiae. Pytochmistry 1992, 31 (11), 3969-3973;
    • (1992) Pytochmistry , vol.31 , Issue.11 , pp. 3969-3973
    • Kubo, S.1    Mimaki, Y.2    Terao, M.3    Sashida, Y.4    Nikaido, T.5    Ohmoto, T.6
  • 8
    • 0032485307 scopus 로고    scopus 로고
    • The first synthesis of the aglycone of the potent antitumor steroidal saponin OSW-1
    • (c) Guo, C.; Fuchs, P.L. The first synthesis of the aglycone of the potent antitumor steroidal saponin OSW-1. Tetrahedron Lett. 1998, 39, 1099-1102;
    • (1998) Tetrahedron Lett. , vol.39 , pp. 1099-1102
    • Guo, C.1    Fuchs, P.L.2
  • 9
    • 0033534604 scopus 로고    scopus 로고
    • First total synthesis of an exceptionally potent antitumor saponin
    • (d) Deng, S.; Yu, B.; Lou, Y.; Hui, Y. First total synthesis of an exceptionally potent antitumor saponin. J. Org. Chem. 1999, 64, 202-208;
    • (1999) J. Org. Chem. , vol.64 , pp. 202-208
    • Deng, S.1    Yu, B.2    Lou, Y.3    Hui, Y.4
  • 10
    • 0035649771 scopus 로고    scopus 로고
    • Synthesis of the potent antitumor saponin OSW-1 aglycone
    • (e) Morzycki, J.W.; Gryszkiewicz, A. Synthesis of the potent antitumor saponin OSW-1 aglycone. Polish J. Chem. 2001, 5, 983-989;
    • (2001) Polish J. Chem. , vol.5 , pp. 983-989
    • Morzycki, J.W.1    Gryszkiewicz, A.2
  • 11
    • 0034829735 scopus 로고    scopus 로고
    • A new strategy for the stereoselective introduction of steroid side chain via α-alkoxy vinyl cuprates: Total synthesis of a highly potent antitumor natural product OSW-1
    • (f) Yu, W.; Jin, Z. A new strategy for the stereoselective introduction of steroid side chain via α-alkoxy vinyl cuprates: total synthesis of a highly potent antitumor natural product OSW-1. J. Am. Chem. Soc. 2001, 123, 3369-3370.
    • (2001) J. Am. Chem. Soc. , vol.123 , pp. 3369-3370
    • Yu, W.1    Jin, Z.2
  • 12
    • 0033844267 scopus 로고    scopus 로고
    • Synthesis of cytostatic pyrazines and a novel reduction-oxidation sequence for spiroketal opening in sapogenins
    • Basler, S.; Brunck, A.; Jautelat, R.; Winterfeldt, E. Synthesis of cytostatic pyrazines and a novel reduction-oxidation sequence for spiroketal opening in sapogenins. Helv. Chim. Acta. 2000, 83, 1854-1879.
    • (2000) Helv. Chim. Acta , vol.83 , pp. 1854-1879
    • Basler, S.1    Brunck, A.2    Jautelat, R.3    Winterfeldt, E.4
  • 13
    • 37049115532 scopus 로고
    • Studies on epoxides. Part III. Epoxidation of allylic alcohols with chromium trioxide
    • Glotter, E.; Greenfield, S.; Lavie, D. Studies on epoxides. Part III. Epoxidation of allylic alcohols with chromium trioxide. J. Chem. Soc. (C) 1968, 1646-1653.
    • (1968) J. Chem. Soc. (C) , pp. 1646-1653
    • Glotter, E.1    Greenfield, S.2    Lavie, D.3
  • 14
    • 0035961113 scopus 로고    scopus 로고
    • Study of the Lewis-acid-promoted rearrangement of 2-aryl-2,3-epoxy acylates
    • Kita, Y.; Furukawa, A.; Futamura, J.; Higuchi, K.; Ueda, K.; Fujioka, H. Study of the Lewis-acid-promoted rearrangement of 2-aryl-2,3-epoxy acylates. Tetrahedron 2001, 57, 815-825.
    • (2001) Tetrahedron , vol.57 , pp. 815-825
    • Kita, Y.1    Furukawa, A.2    Futamura, J.3    Higuchi, K.4    Ueda, K.5    Fujioka, H.6


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.