Synthesis of leprapinic acid, calycine and analogues by sequential "[3+2] cyclization/suzuki/lactonization" reactions

European Journal of Organic Chemistry

Volumn , Issue 16, 2005, Pages 3469-3474

  Ahmed, Zafar ^a,b   Albrecht, Uwe ^b   Langer, Peter ^a  

^a UNIVERSITY OF ROSTOCK   (Germany)

^b UNIVERSITY OF GREIFSWALD   (Germany)

Author keywords

Butenolides; Cyclizations; Heterocycles; Lactones; Leprapinic acid; Natural products

Indexed keywords

EID: 23944434780     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejoc.200500142     Document Type: Article

References (34)

1. Reviews: a) Y. S. Rao, Chem. Rev. 1976, 76, 625;
2. b) G. Pattenden, Prog. Chem. Nat. Prod. 1979, 55, 133;
3. c) M. Gill, W. Steglich, Prog. Chem. Org. Nat. Prod. 1987, 51, 1;
4. d) D.W. Knight, Contemp. Org. Synth. 1994, 1, 287;
5. e) E.-i. Negishi, M. Kotora, Tetrahedron 1997, 53, 6707;
6. for reviews on syntheses of γ-alkylidenebutenolides, see: f) R. Brückner, Chem. Commun. 2002, 141;
7. g) R. Brückner, Curr. Org. Chem. 2001, 5, 679.
8. O. Hesse, Ber. Dtsch. Chem. Ges. 1880, 13, 1816.
9. W. Steglich, W. Furtner, A. Prox, Z. Naturforsch., Teil B 1970, 25, 557.
10. a) R. L. Edwards, G. C. Elsworthy, J. Chem. Soc. D 1967, 373;
11. b) P. C. Beaumont, R. L. Edwards, J. Chem. Soc. C 1968, 2968;
12. c) P. C. Beaumont, R. L. Edwards, J. Chem. Soc. C 1969, 2398;
13. d) W. Steglich, H. Besl, K. Zipfel, Z. Naturforsch., Teil B 1974, 29, 96.
14. S. C. Agarwal, T. R. Seshadri, Tetrahedron 1965, 21, 3205.
15. B. Åkermark, Acta Chem. Scand. 1961, 15, 1695.
16. For syntheses of leprapinic acid, see: a) H. M. Chawla, S. S. Chibber, S. Niwas, Tetrahedron Lett. 1980, 21, 2089;
17. b) R. Ramage, G. J. Griffiths, J. N. A. Sweeney, J. Chem. Soc. Perkin Trans. 1 1984, 1547.
18. a) K. Krohn, H.-H. Ostermeyer, K. Tolkiehn, Chem. Ber. 1979, 112, 2640;
19. b) T.-H. Chan, P. Brownbridge, J. Am. Chem. Soc. 1980, 102, 3534;
20. c) B. Simoneau, P. Brassard, Tetrahedron 1986, 42, 3767;
21. d) G. A. Molander, K. O. Cameron, J. Am. Chem. Soc. 1993, 115, 830.
22. For a review on 1,3-bis(silyl enol ethers) see: P. Langer, Synthesis 2002, 441.
23. a) P. Langer, M. Stoll, Angew. Chem. 1999, 111, 1919;
24. Angew. Chem. Int. Ed. 1999, 38, 1803;
25. b) P. Langer, T. Schneider, M. Stoll, Chem. Eur. J. 2000, 6, 3204.
26. a) P. Langer, T. Eckardt, T. Schneider, C. Göbel, R. Herbst-Irmer, J. Org. Chem. 2001, 66, 2222;
27. b) Z. Ahmed, P. Langer, J. Org. Chem. 2004, 69, 3753;
28. c) Z. Ahmed, P. Langer, Tetrahedron 2005, 61, 2055.
29. M. Desage-El Murr, S. Nowaczyk, T. Le Gall, C. Mioskowski, B. Amekraz, C. Moulin, Angew. Chem. 2003, 115, 1327;
30. Angew. Chem. Int. Ed. 2003, 42, 1289.
31. [l3] For cross-coupling reactions of related butenolides, see: a) K. Siegel, R. Brückner, Chem. Eur. J. 1998, 4, 1116;
32. b) F. Goerth, A. Umland, R. Brückner, Eur. J. Org. Chem. 1998, 1055.
33. P. Pfeiffer, E. Enders, Chem. Ber. 1951, 84, 247.
34. M. P. Sibi, M. Mali, R. Sharma, J. Org. Chem. 1995, 60, 5016.