Synthesis and reactions of functionalized spirocyclopropanes by cyclization of dilithiated β-ketosulfones, α-cyanoacetone and diethyl 2-oxopropylphosphonate with 1,1-diacetylcyclopropane

Tetrahedron

Volumn 64, Issue 14, 2008, Pages 3246-3252

  Rasool, Nasir ^a   Rashid, Muhammad A ^a   Reinke, Helmut ^a   Fischer, Christine ^b   Langer, Peter ^a,b  

^a UNIVERSITY OF ROSTOCK   (Germany)

^b LEIBNIZ INSTITUT FÜR KATALYSE E V AN DER UNIVERSITÄT ROSTOCK   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

1 HYDROXYSPIRO[5.2]CYCLOOCT 4 EN 3 ONE DERIVATIVE; 1,1 DIACETYLCYCLOPROPANE; ACETONE; ALPHA CYANOACETONE; BETA KETOSULFONE DERIVATIVE; CYCLOPROPANE DERIVATIVE; DIETHYL 2 OXOPROPYLPHOSPHONATE; HALIDE; PHENOL DERIVATIVE; PHOSPHONIC ACID DERIVATIVE; SPIROCYCLOPROPANE DERIVATIVE; SULFONE DERIVATIVE; TETRABUTYLAMMONIUM; UNCLASSIFIED DRUG;

ARTICLE; CYCLIZATION; DRUG SYNTHESIS; LITHIATION; PRIORITY JOURNAL;

EID: 39649107329     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2008.01.066     Document Type: Article

References (39)

1. Zips D., Thames H.D., and Baumann M. In Vivo 19 (2005) 1
2. Kim R. Cancer 103 (2005) 1551
3. Kim J., and Park E.J. Curr. Med. Chem. Anti-Cancer Agents 2 (2002) 485
4. Filipits M. Drug Discov. Today 1 (2004) 229
5. Righetti S.C., Gatti L., Beretta G.L., Zunino F., and Perego P. Rec. Res. Dev. Mol. Pharmacol. 1 (2002) 167
6. Saever F.J. J. New York Bot. Gard. (1938) 263
7. Seaver F.J. J. New York Bot. Gard. (1939) 236
8. Nakanishi K., Tada M., Yamada Y., Ohashi M., Komatsu N., and Terekawa H. Nature 197 (1963) 292
9. Anchel M., Hervey A., and Robbins W.J. Proc. Natl. Acad. Sci. U.S.A. 36 (1950) 300
10. McMorris T.C., and Anchel M. J. Am. Chem. Soc. 85 (1963) 831
11. McMorris T.C., and Anchel M. J. Am. Chem. Soc. 87 (1965) 1594
12. Ayer W.A., and Browne L.M. Tetrahedron 37 (1981) 2199
13. McMorris T.C., Kelner M.J., Wang W., Estes L.A., Montoya M.A., and Taetle R. J. Org. Chem. 57 (1992) 6876 For the synthesis of an illudinoid library, see:
14. Pirrung M.C., and Liu H. Org. Lett. 5 (2003) 1983
15. Bryson T.A., and Roth G.A. Tetrahedron Lett. 29 (1988) 2167
16. Boger D.L., and Johnson D.S. J. Am. Chem. Soc. 112 (1990) 5832
17. Boger D.L., Garbaccio R.M., and Jin Q. J. Org. Chem. 62 (1997) 8875
18. Boger D.L., Boyce C.W., Carpaccio R.M., and Goldberg J.A. Chem. Rev. 97 (1997) 787
19. Tietze L.F., Hannemann R., Buhr W., Lögers M., Menningen P., Lieb M., Starck D., Grote T., Döring A., and Schuberth I. Angew. Chem. 108 (1996) 2840
20. Angew. Chem., Int. Ed. 35 (1996) 2674
21. Tietze L.F., Buhr W., Looft J., and Grote T. Chem.-Eur. J. 4 (1998) 1554
22. Baird R., and Winstein S. J. Am. Chem. Soc. 79 (1957) 4238
23. Baird R., and Winstein S. J. Am. Chem. Soc. 85 (1963) 574
24. Woolhouse A.D. Aust. J. Chem. 30 (1977) 1145
25. Schuster D.I., and Polowczyk C.J. J. Am. Chem. Soc. 88 (1966) 1722
26. Phillips J.P., Gillmore J.G., Schwartz P., Brammern Jr. L.E., Berger D.J., and Tanko J.M. J. Am. Chem. Soc. 120 (1998) 195
27. Ward R.S., and Thatcher K.S. Tetrahedron Lett. 22 (1981) 4831
28. Kende A.S., Hebeisen P., Sanfilippo P.J., and Toder B.H. J. Am. Chem. Soc. 104 (1982) 4244
29. Schultz A.G., and Taveras A.G. Tetrahedron Lett. 37 (1996) 5853
30. Padwa A., Curtis E.A., and Sandanayaka V.P. J. Org. Chem. 61 (1996) 73
31. Langer P., and Bose G. Angew. Chem. 115 (2003) 4165
32. Angew. Chem., Int. Ed. 42 (2003) 4033
33. Bose G., Nguyen V.T.H., Ullah E., Lahiri S., Görls H., and Langer P. J. Org. Chem. 69 (2004) 9128
34. Bose G., and Langer P. Tetrahedron Lett. (2004) 3861
35. Bose G., Bracht K., Bednarski P.J., Lalk M., and Langer P. Bioorg. Med. Chem. 14 (2006) 4694
36. Pound M.K., Davies D.L., Pilkington M., Sousa M.M., and Wallis J.D. Tetrahedron Lett. 43 (2002) 1915
37. Langer P., Holtz E., and Saleh N.N.R. Chem.-Eur. J. 8 (2002) 917
38. CCDC-674698 (3b), CCDC-674699 (4f) and CCDC-674700 (7b) contain all crystallographic details of this publication and are available free of charge at www.ccdc.cam.ac.uk/conts/retrieving.html or can be ordered from the following address: Cambridge Crystallographic Data Centre, 12 Union Road, GB-Cambridge CB21EZ; fax: (+44)1223 336 033; or deposit@ccdc.cam.ac.uk.
39. Vinick F.J., Pan Y., and Gschwend H.W. Tetrahedron Lett. 44 (1978) 4221