The Stereochemistry of the Nozaki-Hiyama-Kishi Reaction and the Construction of 10-Membered Lactones. The Enantioselective Total Synthesis of (-)-Decarestrictine D

Journal of the Brazilian Chemical Society

Volumn 12, Issue 3, 2001, Pages 373-385

  Pilli, Ronaldo A ^a   Victor, Mauricio M ^a  

^a UNIVERSITY OF CAMPINAS   (Brazil)

Author keywords

Decanolide; Decarestrictine D; Lactone; Nozaki Hiyama Kishi reaction

Indexed keywords

EID: 0035628576     PISSN: 01035053     EISSN: None     Source Type: Journal    
DOI: 10.1590/S0103-50532001000300009     Document Type: Article

References (52)

1. (a) Grabley, S.; Granzer, E.; Hütter, K.; Ludwig, D.; Mayer, M.; Thiericke, R.; Till, G.; Wink, J.; Phillips, S.; Zeeck, A. J. Antibiotics 1992, 45, 56;
2. (b) Göhrt, A.; Zeeck, A.; Hütter, K.; Kirsch, R.; Kluge, H.; Thiericke, R. J. Antibiotics 1992, 45, 66;
3. (c) Grabley, S.; Hamann, P.; Hütter, K.; Kirsch, R.; Kluge, H.; Mayer, M.; Thiericke, R.; Zeeck, A. J. Antibiotics 1992, 45, 1176;
4. (d) Ayer, W. A.; Sun, M.; Browne, L. M.; Brinen, L. S.; Clardy, J. J. Nat. Prod. 1992, 55, 649.
5. Dräger, D.; Garming, A.; Maul, C.; Noltemeyer, M.; Thiericke, R.; Zerlin, M.; Kirschning, A. Chem. Eur. J. 1998, 4, 1324.
6. Andrus, M. B.; Shih, T.-L. J. Org. Chem. 1996, 61, 8780.
7. For recent reviews see: (a) Dräger, G.; Kirschning, A.; Thiericke, R.; Zerlin, M. Nat. Prod. Rep. 1996, 13, 365; (b) Collins, I. J. Chem. Soc., Perkin Trans. 1 1999, 1377.
8. For recent reviews see: (a) Dräger, G.; Kirschning, A.; Thiericke, R.; Zerlin, M. Nat. Prod. Rep. 1996, 13, 365; (b) Collins, I. J. Chem. Soc., Perkin Trans. 1 1999, 1377.
9. Moore, B. P.; Brown, W. V. Aust. J. Chem. 1976, 29, 1365.
10. Nukina, M.; Sassa, T.; Ikeda, M. Tetrahedron Lett. 1980, 21, 301.
11. Rousseau, G. Tetrahedron 1995, 21, 2777.
12. Pilli, R. A.; Victor, M. M. Tetrahedron Lett. 1998, 39, 4421.
13. For recent reviews see: (a) Wessjohann, L. A.; Scheid, G. Synthesis 1999, 1; (b) Avalos, M.; Babiano, R.; Cintas, P.; Jiménez, J. L.; Palacios, J. C. Chem. Soc. Rev. 1999, 28, 169; (c) Fürstner, A. Chem. Rev. 1999, 99, 991.
14. For recent reviews see: (a) Wessjohann, L. A.; Scheid, G. Synthesis 1999, 1; (b) Avalos, M.; Babiano, R.; Cintas, P.; Jiménez, J. L.; Palacios, J. C. Chem. Soc. Rev. 1999, 28, 169; (c) Fürstner, A. Chem. Rev. 1999, 99, 991.
15. For recent reviews see: (a) Wessjohann, L. A.; Scheid, G. Synthesis 1999, 1; (b) Avalos, M.; Babiano, R.; Cintas, P.; Jiménez, J. L.; Palacios, J. C. Chem. Soc. Rev. 1999, 28, 169; (c) Fürstner, A. Chem. Rev. 1999, 99, 991.
16. (a) Pilli, R. A., de Andrade, C. K. Z.; Souto, C. R. O.; de Meijere, A. J. Org. Chem. 1998, 63, 7811;
17. (b) Oddon, G.; Uguen, D. Tetrahedron Lett. 1998, 39, 1157.
18. Seebach, D.; Brunner, A.; Bachmann, B. M.; Hoffmann, T.; Kühnle, F. N. M.; Lengweiler, U. D. in Biopolymers and -oligomers of (R)-3-Hydroxy-alkanoic Acids, vol. 28, Ernst Schering Research Foundation, Berlin, 1995.
19. (a) Sharpless, H. D.; Amberg, W.; Bennani, Y. L.; Crispino, G. A.; Hartung, J.; Jeong, K.-S.; Kwong, H.-L.; Morikawa, K.; Wang, Z.-M.; Xu, D.; Zang, X.-L. J. Org. Chem. 1992, 57, 2768;
20. (b) Review: Kolb, H. C.; van Nieuwenhze, M. S.; Sharpless, K. B. Chem. Rev. 1994, 94, 2483.
21. Kress, M. H.; Ruel, R.; Miller, W. H.; Kishi, Y. Tetrahedron Lett. 1993, 34, 6003.
22. Schreiber, S. L.; Meyers, H. V. J. Am. Chem. Soc. 1988, 110, 5198.
23. McDougal, P. G.; Rico, J. G.; Oh, Y. I.; Condon, B. D. J. Org. Chem. 1986, 51, 3388.
24. Column: heptakis-(2,6-methyl-3-pentyl)-α-cyclodextrine, 25 m, id 0.25 mm, 20% in OV 1701, FID.
25. Takai, K.; Nitta, K; Utimoto, K. J. Am. Chem. Soc. 1986, 108, 7408.
26. Major isomer (E): δ 6.48 (dd, J 14.5, 0.8 Hz, H5), 6.59 (dd, J 14.5, 5.8 Hz, H4); minor isomer: δ 6.29 (t, J 8.0 Hz, H4), 6.53 (J 8.0, 0.8 Hz, H5).
27. Evans, D. A.; Black, W. C. J. Am. Chem. Soc. 1993, 115, 4497.
28. 4 followed by oxidation of the aldehyde did not provide better yields.
29. 24E: δ 6.22 (dd, J 14.5, 1.8 Hz, H6) and 6.69 (dd, J 14.5, 4.0 Hz, H5).
30. Hodgson, D. M.; Boulton, L. T.; Maw, G. N. Tetrahedron Lett. 1994, 35, 2234.
31. For additional examples of olefination of sterically hindered aldehydes, see: (a) ref. 10a.; (b) Baker, R.; Castro, J. L. J. Chem. Soc., Perkin Trans. 1 1989, 190; (c) Chackalamannil, S.; Davies, R. J.; Asberon, T.; Doller, D.; Leone, D. J. Am. Chem. Soc. 1996, 118, 9812; (d) Williams, D. R.; Kissel, W. S. J. Am. Chem. Soc. 1998, 120, 11198; (e) Fujiwara, K.; Murai, A. J. Am. Chem. Soc. 1998, 120, 10770.
32. For additional examples of olefination of sterically hindered aldehydes, see: (a) ref. 10a.; (b) Baker, R.; Castro, J. L. J. Chem. Soc., Perkin Trans. 1 1989, 190; (c) Chackalamannil, S.; Davies, R. J.; Asberon, T.; Doller, D.; Leone, D. J. Am. Chem. Soc. 1996, 118, 9812; (d) Williams, D. R.; Kissel, W. S. J. Am. Chem. Soc. 1998, 120, 11198; (e) Fujiwara, K.; Murai, A. J. Am. Chem. Soc. 1998, 120, 10770.
33. For additional examples of olefination of sterically hindered aldehydes, see: (a) ref. 10a.; (b) Baker, R.; Castro, J. L. J. Chem. Soc., Perkin Trans. 1 1989, 190; (c) Chackalamannil, S.; Davies, R. J.; Asberon, T.; Doller, D.; Leone, D. J. Am. Chem. Soc. 1996, 118, 9812; (d) Williams, D. R.; Kissel, W. S. J. Am. Chem. Soc. 1998, 120, 11198; (e) Fujiwara, K.; Murai, A. J. Am. Chem. Soc. 1998, 120, 10770.
34. For additional examples of olefination of sterically hindered aldehydes, see: (a) ref. 10a.; (b) Baker, R.; Castro, J. L. J. Chem. Soc., Perkin Trans. 1 1989, 190; (c) Chackalamannil, S.; Davies, R. J.; Asberon, T.; Doller, D.; Leone, D. J. Am. Chem. Soc. 1996, 118, 9812; (d) Williams, D. R.; Kissel, W. S. J. Am. Chem. Soc. 1998, 120, 11198; (e) Fujiwara, K.; Murai, A. J. Am. Chem. Soc. 1998, 120, 10770.
35. For additional examples of olefination of sterically hindered aldehydes, see: (a) ref. 10a.; (b) Baker, R.; Castro, J. L. J. Chem. Soc., Perkin Trans. 1 1989, 190; (c) Chackalamannil, S.; Davies, R. J.; Asberon, T.; Doller, D.; Leone, D. J. Am. Chem. Soc. 1996, 118, 9812; (d) Williams, D. R.; Kissel, W. S. J. Am. Chem. Soc. 1998, 120, 11198; (e) Fujiwara, K.; Murai, A. J. Am. Chem. Soc. 1998, 120, 10770.
36. For additional examples, see: (a) Oikawa, M.; Ueno, T.; Oikawa, H.; Ichihara, A. J. Org. Chem. 1995, 60, 5048; (b) Keck, G. E.; Palani, A.; McHardy, S. F. J. Org. Chem. 1994, 59, 3113.
37. For additional examples, see: (a) Oikawa, M.; Ueno, T.; Oikawa, H.; Ichihara, A. J. Org. Chem. 1995, 60, 5048; (b) Keck, G. E.; Palani, A.; McHardy, S. F. J. Org. Chem. 1994, 59, 3113.
38. (a) ref. 10a;
39. (b) Oikawa, Y.; Tanaka, T.; Hamada, T.; Yonemitsu, O. Chem. Pharm. Bull. 1987, 35, 2196.
40. Evans, P. A.; Roseman, J. D.; Garber, L. T. Synth. Commun. 1996, 26, 4685.
41. Seebach, D,; Züger, M. Helv. Chim. Acta 1982, 65, 495.
42. Still, W. C.; Galynker, I. Tetrahedron 1981, 37, 3981.
43. MacMillan, D. W. C.; Overman, L. E. J. Am. Chem. Soc. 1995, 117, 10391.
44. Inanaga, J.; Hirata, K.; Saeki, H.; Katsuki, T.; Yamaguchi, M. Bull. Chem. Soc. Jpn. 1979, 52, 1989.
45. Secondary to primary acyl migration was observed for alcohol 31.
46. During chromatographic purification and/or storing formation of the corresponding butyrolactone was observed from diol 33.
47. Horita, K.; Yoshioka, T.; Tanaka, T.; Oikawa, Y.; Yonemitsu, O. Tetrahedron 1986, 42, 3021.
48. a) Dess, D. B., Martin, J. C., J. Org. Chem. 1983, 48, 4155;
49. b) Dess, D. B., Martin, J. C., J. Am. Chem. Soc. 1991, 113, 7277;
50. c) Meyer, S. D., Schreiber, S. L. J. Org. Chem. 1994, 59, 7549.
51. Wessjohan, L., Gabriel, T., J. Org. Chem. 1997, 62, 3772.
52. Marshall, J. A., Beadoin, S. J. Org. Chem. 1994, 59, 6614.