A cyclopropanol approach to the synthesis of the C13-C21 fragment of epothilones from diethyl (S)-malate

Tetrahedron Letters

Volumn 46, Issue 41, 2005, Pages 6979-6981

  Bekish, Andrei V ^a   Isakov, Vladimir E ^a   Kulinkovich, Oleg G ^a  

^a BELARUSIAN STATE UNIVERSITY   (Belarus)

Author keywords

(S) Malic acid; Allyl halides; Cyclopropanols; Epothilones

Indexed keywords

BROMINE DERIVATIVE; CARBONYL DERIVATIVE; CYCLOPROPANE; EPOTHILONE DERIVATIVE; ETHYLMAGNESIUM BROMIDE; MALIC ACID DERIVATIVE; PROPANOL; TETRAHYDROPYRAN DERIVATIVE; TITANIUM DERIVATIVE; TITANIUM ISOPROPOXIDE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CYCLOPROPANATION; SYNTHESIS;

EID: 24344495334     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.08.075     Document Type: Article

References (42)

1. O.G. Kulinkovich Chem. Rev. 103 2003 2597 2632
2. D.H. Gibson, and C.H. De Puy Chem. Rev. 74 1974 605 623
3. O.G. Kulinkovich Izv. Akad. Nauk. Ser. Khim. 2004 1022 1043
4. O.G. Kulinkovich Eur. J. Org. Chem. 22 2004 4517 4529
5. Russ. Chem. Bull. (Engl. Transl.) 53 2004 1065 1086
6. O.G. Kulinkovich, and A. De Meijere Chem. Rev. 100 2000 2789 2834
7. F. Sato, H. Urabe, and S. Okamoto Chem. Rev. 100 2000 2835 2886
8. I. Kuwajima, and E. Nakamura Top. Curr. Chem. 133 1990 3 40
9. Bekish, A. V.; Kulinkovich, O. G. Tetrahedron Lett. 2005, 46, in this issue, see doi:10.1016/j.tetlet.2005.08.076.
10. K.C. Nicolaou, F. Roschangar, and D. Vourloumis Angew. Chem., Int. Ed. 37 1998 2014 2045
11. C.R. Harris, and S.J. Danishefsky J. Org. Chem. 64 1999 8434 8456
12. M. Wartmann, and K.-H. Altmann Curr. Med. Chem. Anti-Cancer Agents 2 2002 123 148
13. K.-H. Altmann Minirev. Med. Chem. 3 2003 149 158
14. A. Rivkin, Y.S. Cho, A.E. Gabarda, F. Yoshimura, and S.J. Danishefsky J. Nat. Prod. 67 2004 139 143
15. K.C. Nicolaou, A. Ritzen, and K. Namoto Chem. Commun. 2001 1523 1535
16. K.C. Nicolaou, S. Ninkovic, F. Sarabia, D. Vourloumis, Y. He, H. Vallberg, M.R.V. Finlay, and Z. Yang J. Am. Chem. Soc. 119 1997 7974 7991
17. D. Meng, P. Bertinato, A. Balog, D.-S. Su, T. Kamenecka, E.J. Sorensen, and S.J. Danishefsky J. Am. Chem. Soc. 119 1997 10073 10092
18. K.C. Nicolaou, N. Winssinger, J.A. Pastor, S. Ninkovic, F. Sarabia, Y. He, D. Vourloumis, Z. Yang, T. Li, P. Giannakakou, and E. Hamel Nature 387 1997 268 272
19. R.E. Taylor, and Y. Chen Org. Lett. 3 2001 2221 2224
20. J. Mulzer, A. Mantoulidis, and E. Ohler Tetrahedron Lett. 38 1997 7725 7728
21. J. Mulzer, A. Mantoulidis, and E. Ohler J. Org. Chem. 65 2000 7456 7467
22. E.A. Reiff, S.K. Nair, B.S.N. Reddy, J. Inagaki, J.T. Henri, J.F. Greiner, and G.I. Georg Tetrahedron Lett. 45 2004 5845 5847
23. S.C. Sinha, J. Sun, G. Miller, C.F. Barbas III, and R.A. Lerner Org. Lett. 1 1999 1623 1626
24. B. Zhu, and J.S. Panek Org. Lett. 2 2000 2575 2578
25. B. Zhu, and J.S. Panek Tetrahedron Lett. 41 2000 1863 1866
26. O.G. Kulinkovich, S.V. Sviridov, D.A. Vasilevski, and T.S. Pritytskaya Zh. Org. Khim. 25 1989 2244 2245
27. J. Org. Chem. USSR (Engl. Transl.) 25 1989 2027 2028
28. O.G. Kulinkovich, S.V. Sviridov, and D.A. Vasilevski Synthesis 1991 234
29. J.A. Dale, D.L. Dull, and H.S. Mosher J. Org. Chem. 34 1969 2543 2549
30. 2O).
31. The signals of the protons of the methoxy groups at δ = 3.52 and 3.56 ppm were used to determine the enantiomeric purity.
32. 2O).
33. The use of the corresponding organolithium derivative for alkylation of allyl bromide 5 led to a decrease in the yield of compound 6 due to homocoupling of the starting halogenide.
34. 2S: C, 64.48; H, 7.58. Found: C, 64.71; H, 7.52.
35. 2S: C, 64.48; H, 7.58. Found: C, 64.63; H, 7.54.
36. M. Kirihara, S. Yokoyama, H. Kakuda, and T. Momose Tetrahedron Lett. 36 1995 6907 6910
37. M. Kirihara, S. Yokoyama, H. Kakuda, and T. Momose Tetrahedron 54 1998 13943 13954
38. T. Momose, T. Nishio, and M. Kirihara Tetrahedron Lett. 37 1996 4987 4990
39. 3S: C, 54.75; H, 6.27. Found: C, 54.92; H, 6.18.
40. The (E)-configuration of the acyclic carbon-carbon double bond in compound 8 was verified on the basis of NOE experiments. Irradiation of the olefinic proton of this double bond produced a strong enhancement (15%) of the methine proton signal at δ 4.57-4.64 ppm.
41. The signals of the protons of the methoxy groups at δ = 3.60 and 3.68 ppm were used to determine the enantiomeric purity.
42. 3): δ 1.43-1.88 (m, 6H), 2.02 (d, J = 1.3 Hz, 1.5H), 2.09 (d, J = 1.3 Hz, 1.5H), 2.51-2.63 (m, 1H), 2.69 (s, 1.5H), 2.70 (s, 1.5H), 2.76-2.90 (m, 1H), 3.38-3.56 (m, 1H), 3.74-3.88 (m, 1H), 4.54-4.65 (m, 1H), 4.74-4.83 (m, 1H), 6.54-6.57 (m, 0.5H), 6.59-6.62 (m, 0.5H), 6.95 (s, 0.5H), 6.96 (s, 0.5H), 9.76-9.79 (m, 0.5H), 9.82-9.85 (m, 0.5H).