Synthetic studies of antitumor macrolide laulimalide: Enantioselective synthesis of the C3-C14 segment by a catalytic hetero Diels-Alder strategy

Tetrahedron Letters

Volumn 38, Issue 14, 1997, Pages 2427-2430

  Ghosh, Arun K ^a   Mathivanan, Packiarajan ^a   Cappiello, John ^a  

^a UNIVERSITY OF ILLINOIS AT CHICAGO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC AGENT;

ARTICLE; CATALYSIS; CHEMICAL REACTION; DIASTEREOISOMER; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STEREOCHEMISTRY;

EID: 0030904322     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00416-4     Document Type: Article

References (34)

1. (a) Quinoa, E.; Kakou, Y.; Crews, P. J. Org. Chem. 1988, 53, 3642;
2. (b) Corley, D.G.; Herb, R.; Moore, R.E.; Scheuer, P.J.; paul, V.J. J. Org. Chem. 1988, 53, 3644.
3. (a) Jefford, C.W.; Bernrdinelli, G.; Tanaka, J-I.; Higa, T. Tetrahedron Lett. 1996, 37, 159;
4. (b) Tanaka, J-I.; Higa, T.; Bernrdinelli, G.; Jefford, C.W. Chemistry Lett. 1996, 255.
5. (a) Corey, E.J.; Imai, N.; Zhang, H-Y. J. Am. Chem. Soc. 1991, 113, 728;
6. (b) Corey, E.J.; Isihara, K. Tetrahedron Lett. 1992, 33, 6807;
7. (c) Evans, D.A.; Miller, S.J.; Lectka, T. J. Am. Chem. Soc. 1993, 115, 6460;
8. (d) Evans, D.A.; Murry, J.A.; Mat, P.V.; Norcross, R.D.; Miller, S.J. Angew. Chem. Int. Ed. Engl. 1995, 34, 798;
9. (e) Ghosh, A.K.; Mathivanan, P.; Cappiello, J. Tetrahedron Lett. 1996, 37, 3815;
10. (f) Davies, I.W.; Senanayake, C.H.; Larsen, R.D.; Verhoeven, T.R.; Reider, P.J. Tetrahedron Lett. 1996, 37, 1725;
11. (g) Evans, D.A.; Barnes, D.M. Tetrahedron Lett. 1997, 38, 57;
12. (h) Pfaltz, A. Acta Chimica Scandinavia 1996, 50, 189 and references cited therein.
13. Ghosh A.K., Mathivanan P., Cappiello J., Krishnan K. Tetrahedron: Asymmetry. 7:1996;2615. For other recent catalytic reports, see.
14. (a) Terada, M.; Mikami, K.; Nakai, T. Tetrahedron Lett. 1991, 32, 935;
15. (b) Corey, E.J.; Cywin, C.L.; Roper, T.D. Tetrahedron Lett. 1992, 33, 6907;
16. (c) Gao, Q.; Maruyama, T.; Mouri, M.; Yamamoto, H. J. Org. Chem. 1992, 57, 1957;
17. (d) Mikami, K.; Motoyama, Y.; Terada, M. J. Am. Chem. Soc., 1994, 116, 2811;
18. (e) Motoyama, Y.; Mikami, K. J. Chem. Soc. Chem. Commun. 1994, 1563;
19. (f) Keck, G.E.; Li, X-Y.; Krishnamurthy, D. J. Org. Chem. 1995, 60, 5998.
20. For synthetic application of wide variety of dihydropyranones, see, (a) Danishefsky, S.J. Aldrichim, Acta 1986, 19, 59;
21. (b) Bednarski, M.D.; Lyssikatos, J.P. Comprehensive Organic Synthesis: Selectivity, Strategy and Efficiency in Modern Organic Chemistry, Trost, B.M. Ed., 1991, 2, 661;
22. (c) Meng, D.; Sorensen, E.J.; Bertinato, P.; Danishefsky, S.J. J. Org. Chem. 1996, 61, 7998;
23. (c) Bertinato, P.; Sorensen, E.J.; Meng, D.; Danishefsky, S.J. J. Org. Chem. 1996, 61, 8000;
24. (d) Paterson, I.; Cumming, J.G.; Ward, R.A.; Lambley, Serge. Tetrahderon 1995, 51, 9393 and references cited therein.
25. Available from Aldrich. For recent application in catalytic Mukaiyama aldol reaction, see, Evans, D.A.; Murry, J.A.; Kozlowski, M.C. J. Am. Chem. Soc. 1996, 118, 5815.
26. Paterson I., Osborne S. Tetrahedron Lett. 31:1990;2213. and references cited therein.
27. Bulman Page P.C., Marchington A.P., Graham L.J., Harkin S.A., Wood W.W. Tetrahedron. 49:1993;10369.
28. Details of the determination of ee's and absolute configuration of 8 will be reported in due course.
29. 3 solution. Standard workup and chromatography over silica gel afforded 7 (1.8 g, 62% yield) as a colorless oil.
30. Sirsi W., Padias A.B., Hall H.K. Jr. J. Org. Chem. 49:1984;5424.
31. Toshima, K.; Miyamoto, N.; Matsuo, G.; Nakata, M.; Matsura, S. J. Chem. Soc. Chem. Commun. 1996, 1379.
32. Oppolzer W., Kingma A.J. Helv. Chim. Acta. 72:1989;1337. and references cited therein.
33. Rubottom G.M., Kim C. J. Org. Chem. 48:1983;1550.
34. 3) d: 223.3, 129.9, 124.1, 96.4, 69.4, 65.2, 64.4, 55.1, 52.2, 42.8, 34.5, 31.1, 29.6, 26.5, 19.3.