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Volumn 5, Issue 11, 2003, Pages 1837-1839

Two syntheses of FF-MAS

Author keywords

[No Author keywords available]

Indexed keywords

4,4 DIMETHYL 5ALPHA CHOLESTA 8,14,24 TRIEN 3BETA OL; STEROL DERIVATIVE; UNCLASSIFIED DRUG; 4,4 DIMETHYLCHOLESTA 8,14,24 TRIENOL; 4,4-DIMETHYLCHOLESTA-8,14,24-TRIENOL; CHOLESTANE DERIVATIVE; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; ERGOSTEROL; STEROL;

EID: 0041350420     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0343156     Document Type: Article
Times cited : (6)

References (32)
  • 5
    • 0034023952 scopus 로고    scopus 로고
    • For recent reviews see: (a) Hegele-Hartung, C.; Blume, T.; Lessl, M.; Ottesen, J. L.; Grondahl, C. Reproduktionsmedizin 2000, 16, 129. (b) Byskov, A. G.; Andersen, C. Y.; Leonardsen, L.; Baltsen, M. J. Exp. Zool. 1999, 285, 237. (c) Byskov, A. G.; Baltsen, M.; Andersen, C. Y. J. Mol. Med. 1998, 76, 818.
    • (2000) Reproduktionsmedizin , vol.16 , pp. 129
    • Hegele-Hartung, C.1    Blume, T.2    Lessl, M.3    Ottesen, J.L.4    Grondahl, C.5
  • 6
    • 0033569776 scopus 로고    scopus 로고
    • For recent reviews see: (a) Hegele-Hartung, C.; Blume, T.; Lessl, M.; Ottesen, J. L.; Grondahl, C. Reproduktionsmedizin 2000, 16, 129. (b) Byskov, A. G.; Andersen, C. Y.; Leonardsen, L.; Baltsen, M. J. Exp. Zool. 1999, 285, 237. (c) Byskov, A. G.; Baltsen, M.; Andersen, C. Y. J. Mol. Med. 1998, 76, 818.
    • (1999) J. Exp. Zool. , vol.285 , pp. 237
    • Byskov, A.G.1    Andersen, C.Y.2    Leonardsen, L.3    Baltsen, M.4
  • 7
    • 0031774248 scopus 로고    scopus 로고
    • For recent reviews see: (a) Hegele-Hartung, C.; Blume, T.; Lessl, M.; Ottesen, J. L.; Grondahl, C. Reproduktionsmedizin 2000, 16, 129. (b) Byskov, A. G.; Andersen, C. Y.; Leonardsen, L.; Baltsen, M. J. Exp. Zool. 1999, 285, 237. (c) Byskov, A. G.; Baltsen, M.; Andersen, C. Y. J. Mol. Med. 1998, 76, 818.
    • (1998) J. Mol. Med. , vol.76 , pp. 818
    • Byskov, A.G.1    Baltsen, M.2    Andersen, C.Y.3
  • 18
    • 0141438719 scopus 로고    scopus 로고
    • PCT Int. Appl. WO 2000056758
    • (c) Geisler, J.; Winter, E. PCT Int. Appl. WO 2000056758.
    • Geisler, J.1    Winter, E.2
  • 19
    • 0141550237 scopus 로고    scopus 로고
    • note
    • Strategy of this approach (route A) has been disclosed in a German patent application; see ref 9b.
  • 24
    • 0001755848 scopus 로고
    • Analogous side chain isomerization under iodine catalysis has been described: Kircher, H. W.; Rosenstein, F. U. J. Org. Chem. 1987, 52, 2586.
    • (1987) J. Org. Chem. , vol.52 , pp. 2586
    • Kircher, H.W.1    Rosenstein, F.U.2
  • 25
    • 0023007117 scopus 로고
    • and references therein
    • Diene isomerizations have been described in the literature: Dolle, R. E. ; Kruse L. I. J. Org. Chem. 1986, 51, 4047 and references therein.
    • (1986) J. Org. Chem. , vol.51 , pp. 4047
    • Dolle, R.E.1    Kruse, L.I.2
  • 26
    • 0141773559 scopus 로고    scopus 로고
    • note
    • Isomeric ratio of Δ24:Δ25 in the side chain is approximately 8:1; the ratio of dienes Δ8,14:Δ6,8(14) is approximately 2.5:1, which corresponds to a content of FF-MAS (Δ8,14,24-triene) of ca. 60%.
  • 27
    • 0141438718 scopus 로고    scopus 로고
    • See ref 8b.
    • See ref 8b.
  • 28
    • 0141550236 scopus 로고    scopus 로고
    • note
    • Oocyte assay has been adopted from the literature (see ref 1). Naked oocytes (NO) were punctured from ovaries of mice primed with follicle stimulation hormone. After in vitro culture in the presence of 3 mM hypoxanthine and 10 μM of the corresponding test compounds for 15-24 h, germinal vesicle breakdown (GVB) and polarbody (PB) values are measured. The values for GVB and PB are comparable to the data reported in the literature.
  • 29
    • 0141773560 scopus 로고    scopus 로고
    • note
    • Commercially available from Research: 10 g costs ca. $300 $.
  • 32
    • 0141773558 scopus 로고    scopus 로고
    • Eur. Pat. Appl. EP 1245572, 2002
    • For the synthesis of analogues with enhanced biological activity in the cumulus-enclosed oocyte assay based on route B, see: Blume, T.; Esperling, P.; Hegele-Hartung, C. Eur. Pat. Appl. EP 1245572, 2002.
    • Blume, T.1    Esperling, P.2    Hegele-Hartung, C.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.