A new route to stereoselective construction of 6β,7β-methylene unit from androst-5-en-7-one

Tetrahedron

Volumn 63, Issue 22, 2007, Pages 4630-4635

  Deng, Gang ^a   Li, Zheng ^a   Peng, Shu Ying ^a   Fang, Li ^a   Li, Yuan Chao ^a  

^a SHANGHAI INSTITUTE OF MATERIA MEDICA   (China)

Author keywords

6 ,7 Methylene unit; Stereoselective; Synthesis; Winstein cyclization

Indexed keywords

3BETA,17BETA BIS(TERT BUTYLDIMETHYLSILYLOXY)ANDROST 5 EN 7 ONE; 6BETA,7BETA METHYLENE; ANDROST 5 EN 7 ONE; STEROID; UNCLASSIFIED DRUG;

ARTICLE; CYCLIZATION; CYCLOPROPANATION; GRIGNARD REACTION; OXIDATION; PRIORITY JOURNAL; STEREOCHEMISTRY;

EID: 34247517383     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2007.03.110     Document Type: Article

References (27)

1. Costantino, F.; Lenna, R.; Piuri, S. U.S. Patent 20,050,192,450, 2005;
2. Tankó L.B., and Christiansen C. J. Intern. Med. 258 (2005) 544
3. Fuhrmann U., Krattenmacher R., Slater E.P., and Fritzemeier K.-H. Contraception 54 (1996) 243
4. Bittler D., Hofmeister H., Laurent H., Nickisch K., Nickolson R., Petzoldt K., and Wiechert R. Angew. Chem. 94 (1982) 718
5. Sitruk-Ware R. Hum. Reprod. Update 12 (2006) 169
6. Krattenmacher R. Contraception 62 (2000) 29
7. Sitruk-Ware R. Climacteric 8 (2005) 4
8. Elger W., Beier S., Pollow K., Garfield R., Shi S.Q., and Hillisch A. Steroids 68 (2003) 891
9. Oelkers W. Mol. Cell. Endocrinol. 217 (2004) 255
10. Sillem M., Schneidereit R., Heithecker R., and Mueck A.O. Eur. J. Contracept. Reprod. Health Care 8 (2003) 162
11. Stanczyk F.Z. Rev. Endocr. Metab. Disord. 3 (2002) 211
12. Dyson N.H., Edwards J.A., and Fried J.H. Tetrahedron Lett. 7 (1966) 1841
13. Kamata S., Matsui T., Haga N., Nakamura M., Odaguchi K., Itoh T., Shimizu T., Suzuki T., Ishibashi M., Yamada F., and Katoh G. J. Med. Chem. 30 (1987) 1647
14. Kohout L., and Fajkoš J. Collect. Czech. Chem. Commun. 40 (1975) 3924
15. Wiechert R. Angew. Chem., Int. Ed. Engl. 6 (1967) 799
16. Baird R., and Winstein S. J. Am. Chem. Soc. 85 (1963) 567
17. Boger D.L., and Coleman R.S. J. Am. Chem. Soc. 110 (1988) 1321
18. Boger D.L., and Turnbull P. J. Org. Chem. 63 (1998) 8004
19. Zheng Y.-H., and Li Y.-C. J. Org. Chem. 68 (2003) 1603
20. Gu Q., Zheng Y.-H., and Li Y.-C. Synthesis 2006 (2006) 975
21. Tamao K., Ishida N., Ito Y., Kumada M., Tran V.D., and Overman L.E. Org. Synth. 69 (1990) 96
22. Kursanov D.N., Parnes Z.N., and Liim N.M. Synthesis 1974 (1974) 633
23. Adlington M.G., Orfanopoulos M., and Fry J.L. Tetrahedron Lett. 17 (1976) 2955
24. Tedesco R., Fiaschi R., and Napolitano E. J. Org. Chem. 60 (1995) 5316
25. Peters R.H., Crowe D.F., Avery M.A., Chong W.K.M., and Tanabe M. J. Med. Chem. 32 (1989) 2306
26. Lau C.K., Dufresne C., Bélanger P.C., Piétré S., and Scheigetz J. J. Org. Chem. 51 (1986) 3038
27. Oppenauer R.V. Recl. Trav. Chim. Pays-Bas 56 (1937) 137