Facile synthesis of a steroidal diyne via D-ring cleavage

Tetrahedron Letters

Volumn 38, Issue 38, 1997, Pages 6749-6750

  Ahmed, Shahadat ^a   Boruah, Romesh Chandra ^a  

^a REGIONAL RESEARCH LABORATORY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENYLDIALKYNE DERIVATIVE; ANTINEOPLASTIC ANTIBIOTIC; STEROID; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL MODIFICATION; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0030805965     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01543-8     Document Type: Article

References (30)

1. a) Goldberg, I.H. Acct. Chem. Res., 1991, 24, 191-198.
2. b) Hensens, O.D.; Giner, J.L.; Goldberg, I.H. J. Am. Chem. Soc., 1989, 111, 3295-3299.
3. c) Chin, D.H.; Tseng, M.C. Tetrahedron Lett., 1997, 38, 2891-2894.
4. d) Golik, J.; Clardy, J.; Dubay, G.; Groenewold, G.; Kawaguchi, H.; Konishi, M.; Krishnan, B.; Ohkuma, H.; Saitoh,K.; Doyle, T.W. J.Am.Chem.Soc., 1987, 109, 3461-3162.
5. a) Lee, M.D.; Dunne, T.S.; Chang,C.C.; Ellestad,G.A.; Seigel,M.M.; Morton,G.O.; McGahren,W.J.; Borders,D.B. J.Am.Chem.Soc., 1987, 109, 3466-3468.
6. b) Nishikawa,T.;.; Ino,A.; Isobe,M. Tetrahedron, 1994, 50, 1449-1468.
7. c) Leet,J.E.; Schroeder,D.R.; Hofstead,S.J.; Golik,J.; Colson,K.L.; Huang,S.; Klohr,S.E. Doyle,T.W.; Matson,J.A. J.Am.Chem.Soc. 1992, 114, 7946-7948.
8. Kedow J.F., Cook D.J., Doyle T.W., Langley D.R., Pham K.M., Vyas D.M., Wittman M.D. Tetrahedron. 50:1994;1519-1538.
9. a) Yoshida,K.; Minami, Y.; Azuma,R.; Saeki,M.; Otani,T. Tetrahedron Lett., 1993, 34, 2637-2640.
10. b)Hensens,O.D.; Helms,G.L.; Zink,D.L.; Chin,D.H.; Kappen,L.S.; Goldberg, I.H. J.Am.Chem.Soc., 1993, 115, 11030-11031.
11. c) Eckhardt,M.; Bruckner,R.; Suffert,J. Tetrahedron Lett. 1995, 36, 5167-5170.
12. a) Bunnage,M.E.; Nicalao,K.C. Angew. Chem. Int. Ed. Engl., 1996, 35, 1110-1112.
13. b) Taunton,J.; Wood,J.L.; Schreiber,S.L. J.Am.Chem.Soc., 1993, 115, 10378-10379.
14. c) Hirama,M.; Gombuchi,T.; Fujiwara,K. J.Am.Chem.Soc.; 1991, 113, 9851-9853.
15. a) Wender,P.A.; McKinney,J.A.; Mukai,C. J.Am.Chem.Soc., 1990, 112,5369-5370.
16. b)Fujiwara,K.; Kurisaki A.; Hirama,M. Tetrahedron Lett., 1990, 31, 4329-4332.
17. c) Wender,P.A.; Tebbe,M.J. Tetrahedron, 1994, 50, 1419-1434.
18. a) Wang,J.; De Clercq,P.J. Angew.Chem.Int.Ed.Engl., 1995, 34, 1749-1752.
19. b) Wang,J.; De Clercq,P.J. Tetrahedron Lett., 1996, 37, 3395-3398.
20. c) Meert,C.; Wang,J.; De Clercq,P.J. Tetrahedron Lett., 1997, 38, 2179-2192.
21. Ahmed S., Boruah R.C. Tetrahedron Lett. 37:1996;8231-8232.
22. Hong,C.I. in 'Antitumor Steroids' by Blikenstaff,R.T., academic Press, New York, 1992, 155-174.
23. a) Jiang,H.; Ma,S.; Zhu,G.; Lu,X. Tetrahedron, 1996, 52, 10945-10954.
24. b) Herault,X.; McNelis,E. Tetrahedron, 1996, 52, 10267-10278.
25. c) Stille,J.K. Angew.Chem.Int.Ed.Engl., 1986, 25, 508-524.
26. a) Denmark,S.E. in 'Comprehensive Organic Synthesis' Ed. Trost,B.M., Pergamon Press, Vol-5, 1991, 770-771.
27. b) Hiyama,T.; Shinoda, M.; Nozaki, H. Tetrahedron Lett., 1978, 771-774.
28. Ahmed S., Boruah R.C. Tetrahedron Lett. 38:1997;1845-1846.
29. 3COOH), 33%].
30. Pakulski Z., Zamojski A. Tetrahedron. 53:1997;2653-2666.