The first synthesis of an A-ring fused steroidal isothiazole
A simple and efficient route to A-ring fused steroidal isothiazoles was developed. The key step involves C-S bond formation via substitution of a vinyl triflate at C-3. © 1994.
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1994
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| LEADER | 05953caa a22007697a 4500 | ||
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| 001 | PAPER-69 | ||
| 003 | AR-BaUEN | ||
| 005 | 20230518202927.0 | ||
| 008 | 190411s1994 xx ||||fo|||| 00| 0 eng|d | ||
| 024 | 7 | |2 scopus |a 2-s2.0-0027932756 | |
| 040 | |a Scopus |b spa |c AR-BaUEN |d AR-BaUEN | ||
| 030 | |a TELEA | ||
| 100 | 1 | |a Giacopello, S. | |
| 245 | 1 | 4 | |a The first synthesis of an A-ring fused steroidal isothiazole |
| 260 | |c 1994 | ||
| 270 | 1 | 0 | |m Giacopello, S.; Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, 1428 Buenos Aires, Argentina |
| 506 | |2 openaire |e Política editorial | ||
| 504 | |a Alivizatos, On, (1993) Anti Cancer Drugs, 4, p. 301 | ||
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| 504 | |a Ichikawa, Akimoto, Shimazaki, (1993) Endocrine Journal, 40, p. 425 | ||
| 504 | |a Juniewicz, Hoekstra, Lemp, Barbolt, Devin, Gauthier, Frenette, Tremblay, (1993) Endocrinology, 133, p. 904 | ||
| 504 | |a Stinson, Prostate drug Proscar cleared for marketing (1992) Chemical & Engineering News, 29, p. 7 | ||
| 504 | |a Snyder, Winneker, Batzold, (1989) J. Steroid Biochem., 33, p. 1127 | ||
| 504 | |a Mallamo, Pilling, Wetzel, Kowalczyk, Bell, Kullnig, Batzold, Winneker, (1992) J. Med. Chem., 35, p. 1663 | ||
| 504 | |a Kumar, Daum, Bell, Alexander, Christiansen, Ackerman, Krolski, Wagner, (1991) Tetrahedron, 47, p. 5099 | ||
| 504 | |a Kumar, Bell, (1992) Heterocycles, 34, p. 1289 | ||
| 504 | |a Suschitzky, Scriven, (1992) Progress in Heterocyclic Chemistry, 4. , Pergamon Press | ||
| 504 | |a Suschitzky, Scriven, (1993) Progress in Heterocyclic Chemistry, 5. , Pergamon Press | ||
| 504 | |a Schulze, Mütze, Selke, Kempe, (1993) Tetrahedron Lett., 34, p. 1909 | ||
| 504 | |a Mander, Sethi, (1983) Tetrahedron Lett., 24, p. 5425 | ||
| 504 | |a Ziegler, Stirchak, Wester, (1986) Tetrahedron Lett., 27, p. 1229 | ||
| 504 | |a Childs, Weber, (1976) J. Org. Chem., 41, p. 3486 | ||
| 504 | |a Stang, Hanck, Subramanian, Perfluoroalkanesulfonic Esters: Methods of Preparation and Applications in Organic Chemistry (1982) Synthesis, p. 85 | ||
| 504 | |a Lee, Snyder, (1990) J. Org. Chem., 55, p. 4995 | ||
| 504 | |a McMurry, Scott, (1980) Tetrahedron Lett., 21, p. 4313 | ||
| 504 | |a Brückner, Scheuplein, Suffert, (1991) Tetrahedron Lett., 32, p. 1449 | ||
| 504 | |a Beard, Baum, Grakauskas, (1973) J. Org. Chem., 38, p. 3673. , Tetrahydrofuran must not be employed as a solvent in this reaction because it reacts with trifluoromethanesulfonic anhydride, or leads to polymerization | ||
| 504 | |a Smith, Trott, (1956) C.A., 50, p. 13982. , U.S. Patent 2732398 (1956) | ||
| 504 | |a A solution of 2-carboxymethyl-3-trifluoromethansulfonyloxy-5α-cholest-2-eno (IV) (1.44 g, 2.51 mmol) in ethanethiol (40 ml) was added to a suspension of sodium thioethoxide (9.74 g, 116 mmol) in ethanethiol (34.5 ml). The reaction mixture was kept at room temperature for 15 hs. After dilution with ethyl acetate, the mixture was washed with 1N NaOH and water. The dried (MgSO4) extract was evaporated and the residue was purified by flash chromatography to give pure thioenolether V (1.16 g, 95%); Cha, Kwon, (1987) J. Org. Chem., 52, p. 5486 | ||
| 504 | |a Mancuso, Huang, Swern, (1978) J. Org. Chem., 43, p. 2480 | ||
| 504 | |a Kimura, Fujita, Ando, Sonochemical activation of manganese dioxide. (1988) Chemistry Letters, p. 1387 | ||
| 504 | |a McKinnon, Lee, Fused heterocycles fromo-acylbenzenethiol derivatives (1988) Canadian Journal of Chemistry, 66, p. 1405 | ||
| 504 | |a Compound I was characterized: m.p.: 109.5–110°C (from methanol); [α]D: +61.0° (c=1.3, CHCl3); 1H-NMR (200 MHz, CDCl3) δ 0.69(3H,s,18-Me); 0.74(3H,s,19-Me); 0.87(6H,d,J=6.6 Hz, 26-Me y 27-Me); 0.92 (3H,d,J=6.4 Hz, 21-Me) ; 2.22 (1H,d,J=15.8 Hz, 1α-H); 2.44 (1H,ddd,J=17.6,11.1,2.0 Hz,4β-H); 2.78(1H,d,J=15.7 Hz,1β-H); 2.83(1H,dd,J=17.7,4.5 Hz,4α-H); 8,16(1H,s,2′-H); 13C-NMR (50 MHz, CDCl3) δ 11.6(C-19); 12.0(C-18); 18.7(C-21); 21.1(C-11); 22.5(C-26); 22.8(C-27); 23.8(C-23); 24.2(C-15); 27.8(C-4); 28.0(C-25); 28.2(C-16); 28.8(C-6); 31.6(C-7); 35.6(C-8); 35.8(C-10 y C-20); 36.2(C-22); 37.1(C-1); 39.5(C-24); 39.9(C-12); 42.4(C-13); 42.5(C-5); 53.7(C-9); 56.3(C-14 y C-17); 133.2(C-2); 157.3(C-3); 157.8(C-2′) | ||
| 520 | 3 | |a A simple and efficient route to A-ring fused steroidal isothiazoles was developed. The key step involves C-S bond formation via substitution of a vinyl triflate at C-3. © 1994. |l eng | |
| 593 | |a Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, 1428 Buenos Aires, Argentina | ||
| 690 | 1 | 0 | |a ANTIANDROGENS |
| 690 | 1 | 0 | |a C-S BOND FORMATION |
| 690 | 1 | 0 | |a PROSTATE CANCER. |
| 690 | 1 | 0 | |a STEROIDAL ISOTHIAZOLES |
| 690 | 1 | 0 | |a VINYL TRIFLATES |
| 690 | 1 | 0 | |a ANTIANDROGEN |
| 690 | 1 | 0 | |a STEROID |
| 690 | 1 | 0 | |a THIAZOLE DERIVATIVE |
| 690 | 1 | 0 | |a ARTICLE |
| 690 | 1 | 0 | |a DRUG SYNTHESIS |
| 690 | 1 | 0 | |a REACTION ANALYSIS |
| 700 | 1 | |a Deluca, M.E. | |
| 700 | 1 | |a Seldes, A.M. | |
| 773 | 0 | |d 1994 |g v. 35 |h pp. 6643-6646 |k n. 36 |p Tetrahedron Lett. |x 00404039 |w (AR-BaUEN)CENRE-415 |t Tetrahedron Letters | |
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| 856 | 4 | 0 | |u https://doi.org/10.1016/S0040-4039(00)73456-3 |y DOI |
| 856 | 4 | 0 | |u https://hdl.handle.net/20.500.12110/paper_00404039_v35_n36_p6643_Giacopello |y Handle |
| 856 | 4 | 0 | |u https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00404039_v35_n36_p6643_Giacopello |y Registro en la Biblioteca Digital |
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| 963 | |a VARI | ||
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