Stereoselective construction of a steroid 5α,7α-oxymethylene derivative and its use in the synthesis of eplerenone
Tài liệu tham khảo
Rabasseda, 1999, Eplerenone: antihypertensive treatment of heart failure aldosterone antagonist, Drugs Future, 24, 488, 10.1358/dof.1999.024.05.526908
Weinberger, 2004, Eplerenone: a new selective aldosterone receptor antagonist, Drugs Today, 40, 481, 10.1358/dot.2004.40.6.850481
Pearlman, 2006, A new approach to the furan degradation problem involving ozonolysis of the trans-enedione and its use in a cost-effective synthesis of eplerenone, Org Lett, 8, 2111, 10.1021/ol060503v
Wuts, 2008, A chemobiological synthesis of eplerenone, Synlett, 418, 10.1055/s-2008-1032064
Wuts, 2007, Stereoselective alkylation of 7-hydroxy-DHEA derivatives, Synlett, 2185, 10.1055/s-2007-984908
Ng JS, Wang PT, Baez JA. Processes for preparation of 9,11 expoxy steroids and intermediates useful therein. US 6953851 B2; 2005.
White MJ, Wuts PGM, Beck D, Wuts PG, White M, Wuts P, et al. New 7-β-hydroxy steroids, 11-α-hydroxy steroids and 7-β,11-α-dihydroxy steroids useful as intermediates for the manufacture of pharmaceutically active steroids, e.g. aldosterone receptor antagonists. WO2004016640-A3; 2004.
Grob J, Kalvoda J. 20-Spiroxanes and analogs with open ring E. EP122232; 1984.
Grob, 1997, Steroidal, aldosterone antagonists. Increased selectivity of 9 α,11-epoxy derivatives, Helv Chim Acta, 80, 566, 10.1002/hlca.19970800220
Grunwell, 1976, Antiprogestational agents. The synthesis of 7-alkyl steroidal ketones with anti-implantational and antidecidual activity, Steroids, 27, 759, 10.1016/0039-128X(76)90136-7
Yamamoto, 1978, RCu·BF3. 3. Conjugate addition to previously unreactive substituted enoate esters and enoic acids, J Am Chem Soc, 100, 3240, 10.1021/ja00478a060
Tamao, 1990, Nucleophilic hydroxymethylation of carbonyl compounds: 1-(hydroxymethyl)cyclohexanol, Org Synth, 69, 96
Smitrovich, 1998, Copper-mediated substitution reactions of alkylmagnesium reagents with allylic carbamates: (Z)-selective alkene synthesis, J Am Chem Soc, 120, 12998, 10.1021/ja9820341
Mello, 2007, A simple protocol for the generation of methyl(trifluoromethyl)dioxirane, Synlett, 2007, 0047, 10.1055/s-2006-958422
Ng JS, Liu C, Anderson DK, Lawson JP, Wieczorek J, Kunda SA, et al. Processes for preparation of 9,11-epoxy steroids and their intermediates. WO9825948; 1998. p. 261–6.
Tamao, 1983, Silafunctional compounds in organic synthesis. 20. Hydrogen peroxide oxidation of the silicon-carbon bond in organoalkoxysilanes, Organometallics, 2, 1694, 10.1021/om50005a041
Cainelli, 1961, Über Steroide und Sexualhormone. 221. Mitteilung. Weitere Oxydationsversuche von 20-Hydroxysteroiden mit Blei(IV)-acetat, Helv Chim Acta, 44, 518, 10.1002/hlca.19610440222
Plietker, 2005, Selectivity versus reactivity – recent advances in RuO4-catalyzed oxidations, Synthesis, 2005, 2453, 10.1055/s-2005-872172
Shimizu, 2005, Ruthenium(salen)-catalyzed aerobic oxidative desymmetrization of meso-diols and its kinetics, J Am Chem Soc, 127, 5396, 10.1021/ja047608i
