Stereoselective halogenation of the 16-hydroxymethyl-3-methoxy-13α-estra-1,3,5(10)-trien-17-ols and their solvolytic investigation

Steroids

Volumn 68, Issue 5, 2003, Pages 451-458

  Wölfling, János ^a   Mernyák, Erzsébet ^a   Forgó, Péter ^a   Schneider, Gyula ^a  

^a UNIVERSITY OF SZEGED   (Hungary)

Author keywords

13 Estrone; D Secosteroid; Selective synthesis; Steroid

Indexed keywords

16ALPHA HYDROXYMETHYL 3 METHOXY 13ALPHA ESTRA 1,3,5(10) TRIEN 17BETA OL; 16BETA HYDROXYMETHYL 3 METHOXY 13ALPHA ESTRA 1,3,5(10) TRIEN 17ALPHA OL; ALCOHOL DERIVATIVE; UNCLASSIFIED DRUG;

ALKALINITY; ARTICLE; HALOGENATION; LYSIS; STEREOCHEMISTRY;

STAPHYLOCOCCUS PHAGE 3A;

EID: 0037530369     PISSN: 0039128X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0039-128X(03)00048-5     Document Type: Article

References (21)

1. Schönecker B., Lange C., Kötteritzsch M., Günther W., Weston J., Anders E.et al. Conformational design for 13α-steroids. J. Org. Chem. 65:2000;5487-5497.
2. Schneider G, Vass A, Vincze I, Sohár P. Neighbouring group participation in the 16-hydroxymethyl-3-methoxyestra-1,3,5(10)-trien-17β-ol series. Liebigs Ann Chem 1988:267-73.
3. Schneider G, Bottka S, Hackler L, Wölfling J, Sohár P. Neighbouring group participation and fragmentation during the solvolysis of the epimers of 3-methoxy-16-(tolylsulfonyloxymethyl)-estra-1,3,5(10)-trien-17-ol. Liebigs Ann Chem 1989:263-7.
4. Capon B, McManus SP. Neighbouring group participation, vol. 1. Plenum Press: New York; 1976. p. 125.
5. Wölfling J, Frank É, Schneider G, Bes MT, Tietze LF. Synthesis of azasteroids and D-homo-steroids by intramolecular cyclization reactions of steroid arylimines. Synlett 1998:1205-6.
6. Grob C.A., Schiess P.W. Die heterolytische fragmentierung als reaktionstypus in der organischen Chemie. Angew. Chemie. 79:1967;1-14.
7. Wölfling J., Frank É., Mernyák E., Bunkóczi G., Cuesta Seijo J.A., Schneider G. Synthesis of novel halogen-containing D-homoestrone and 13α-D-homoestrone derivatives by Lewis acid-induced intramolecular Prins reaction. Tetrahedron. 58:2002;6851-6861.
8. Wölfling J., Mernyák E., Frank É., Falkay G., Márki Á., Minorics R.et al. Synthesis and receptor-binding examinations of the normal- and 13-epi-D-homoestrones and their 3-methyl ethers. Steroids. 68:2003;277-288.
9. Schaub R.E., Kissman H.M., Weiss M.J. The synthesis of certain 16α-substituted derivatives of the 3-methyl ethers of 16β-cyanoestrone and 16β-cyanoestradiol. J. Org. Chem. 29:1964;2775-2777.
10. Allen G.R., Weiss M.J. The reaction of alkoxalylated steroid ketones with dibenzoyl peroxide. A synthesis of 16β-hydroxytestosterone. J. Org. Chem. 27:1962;4681-4682.
11. Ellis B, Patel D, Petrow V. Modified steroid hormones. Part VIII. Some 16-bromo- and 16-chloro-derivatives of testosterone. J Chem Soc 1958:800-4.
12. Fishman J., Biggerstaff W.R. Synthesis of 1,3,5(10)-estratriene-3,16β,17α-triol. J. Org. Chem. 23:1958;1190-1192.
13. 1,3,5-estratrien-17-one and related compounds. J. Org. Chem. 22:1957;1220-1222.
14. Fajkos J. The configuration of some 16-bromo derivatives of androstane. Coll. Czech. Chem. Commun. 20:1955;312-334.
15. Nambara T., Kudo T., Hosoda H., Motojima K., Goya S. Conformational analysis of epimeric 16-bromo-13α-estrones. Chem. Pharm. Bull. 17:1969;2366-2370.
16. Barry C.N., Evans S.A. Triphenylphosphine-tetrachloromethane promoted chlorination and cyclodehydration of simple diols. J. Org. Chem. 46:1981;3361-3364.
17. Duenas J., Garcia-Granados A., Martinez A., Onorato E., Parra A. Opening of ring C in ruthenium-catalyzed rearrangements of 15,16-epoxybeyerane diterpenes hydroxylated at C-12. J. Org. Chem. 60:1995;2170-2173.
18. Sohár P, Fürjes A, Wölfling J, Schneider G. Stereoselective synthesis and determination of the C-16 configuration of 16-halomethyl/16-hydroxymethyl steroids. Synthesis 1992:1280-3.
19. Lange G., Gottardo C. Facile inversion of primary and secondary alcohols to alkyl iodides. Synth. Commun. 20:1990;1473-1479.
20. Vincze I, Somlai C, Schneider G, Dombi G. 15-(Hydroxymethyl)androstene and -estratriene derivatives. Liebigs Ann Chem 1988:973-8.
21. Adam G, Schreiber K. Konfiguration und Umsetzungen von 20-stereoisomeren 20-chlor-16β-hydroxy-pregnanen. Heterolytische Fragmentierung zu 16,17-Secosteroidaldehyden. Liebigs Ann Chem 1967:191-202.