Asymmetric synthesis of (-)-adaline

Organic Letters

Volumn 4, Issue 15, 2002, Pages 2469-2472

  Itoh, Toshimasa ^a   Yamazaki, Naoki ^a   Kibayashi, Chihiro ^a  

^a TOKYO UNIVERSITY OF PHARMACY AND LIFE SCIENCES   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ADALININE; ALKALOID; BRIDGED COMPOUND; CARBROMAL; PIPERIDINE DERIVATIVE; PIPERIDONE DERIVATIVE;

ANIMAL; ARTICLE; BEETLE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

ALKALOIDS; ANIMALS; BEETLES; BRIDGED COMPOUNDS; PIPERIDINES; PIPERIDONES; STEREOISOMERISM;

EID: 0012814538     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0200807     Document Type: Article

References (36)

1. (a) Yamazaki, N.; Ito, T.; Kibayashi, C. Tetrahedron Lett. 1999, 40, 739-742.
2. (b) Yamazaki, N.; Ito, T.; Kibayashi, C. Org. Lett. 2000, 2, 465-467.
3. (c) Yamazaki, N.; Dokoshi, W.; Kibayashi, C. Org. Lett. 2001, 3, 193-196.
4. Yamazaki, N.; Atobe, M.; Kibayashi, C. Tetrahedron Lett. 2001, 42, 5029-5032.
5. For isolation and structure elucidation, see: Lognay, G.; Hemptinne, J. L.; Chan, F. Y.; Gaspar, C. H.; Marlier, M.; Braekman, J. C.; Daloze, D.; Pasteels, J. M. J. Nat. Prod. 1996, 59, 510-511.
6. For a recent review of the coccinellid alkaloids, see: King, A. G.; Meinwald, J. Chem. Rev. 1996, 96, 1105-1122.
7. For the isolation and structural determination of adaline, see: Tursch, B.; Braekman, J. C.; Daloze, D.; Hootele, C.; Losman, D.; Karlsson, R.; Pasteels, J. M. Tetrahedron Lett. 1973, 201-202.
8. For the determination of the absolute configuration of natural (-)-adaline, see: Tursch, B.; Chome, C.; Braekman, J. C.; Daloze, D. Bull. Soc. Chim. Belg. 1973, 82, 699-703.
9. Laurent, P.; Lebrun, B.; Braekman, J.-C.; Daloze, D.; Pasteels, J. M. Tetrahedron 2001, 57, 3403-3412.
10. For the synthesis of (-)-adaline, see: (a) Hill, R. K.; Renbaum, L. A. Tetrahedron 1982, 38, 1959-1963.
11. (b) Yue, C.; Royer, J.; Husson, H.-P. J. Org. Chem. 1992, 57, 4211-4214.
12. For the synthesis of (±)-adaline, see: (c) Alder, v. K.; Betzing, H.; Kuth, R.; Dortmann, H.-A. Liebigs Ann. Chem. 1959, 620, 73-87.
13. (d) Gnecco Medina, D. H.; Grierson, D. S.; Husson, H.-P. Tetrahedron Lett. 1983, 24, 2099-2102.
14. (e) Gössinger, E.; Witkop, B. Monatsh. Chem. 1980, 111, 803-811.
15. (f) Davison, E. C.; Holmes, A. B.; Forbes, I. T. Tetrahedron Lett. 1995, 36, 9047-9050.
16. Myers, A. G.; Yang, B. H.; Kopecky, D. J. Tetrahedron Lett. 1996, 37, 3623-3626.
17. Beumel, O. F., Jr.; Harris, R. F. J. Org. Chem. 1964, 29, 1872-1976.
18. Treatment of 7 with vinylmagnesium bromide or vinyllithium in THF resulted in no reaction.
19. Chiral HPLC (Chiralpak AD column) analysis of compound 14 showed two peaks with exactly equal integration for the both enantiomers.
20. For a review on the reactions and synthetic application of bicyclic lactams containing N,O-acetals, see: Romo, D.; Meyers, A. I. Tetrahedron 1991, 47, 9503-9569.
21. For reviews, see: (a) Grubbs, R. H.; Miller, S. J.; Fu, G. C. Acc. Chem. Res. 1995, 28, 446-552.
22. (b) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413-4450.
23. (a) Fu, G. C.; Nguyen, S. T.; Grubbs, R. H. J. Am. Chem. Soc. 1993, 115, 9856-9857.
24. (b) Suzuki, H.; Yamazaki, N.; Kibayashi, C. Tetrahedron Lett. 2001, 42, 3013-3015.
25. Schwab, P.; Grubbs, R. H.; Ziller, J. W. J. Am. Chem. Soc. 1996, 118, 100-110.
26. (a) Forbes, M. D. E.; Patton, J. T.; Myers, T. L.; Maynard, H. D.; Smith, D. W., Jr.; Schulz, G. R.; Wagener, K. B. J. Am. Chem. Soc. 1992, 114, 10978-10980.
27. (b) Miller, S. J.; Kim, S.-H.; Chen, Z.-R.; Grubbs, R. H. J. Am. Chem. Soc. 1995, 117, 2108-2109.
28. (c) Marsella, M. J.; Maynard, H. D.; Grubbs, R. H. Angew. Chem., Int. Ed. Engl. 1997, 36, 1101-1103.
29. For reviews, see: (a) Johnson, F. Chem. Rev. 1968, 68, 375-413.
30. (b) Hoffmann, R. W. Chem. Rev. 1989, 89, 1841-1860.
31. After completion of our own work, a similar RCM approach to bridged azabicyclic structures was reported by Martin et al.; see: Neipp, C. E.; Martin, S. F. Tetrahedron Lett. 2002, 43, 1779-1782.
32. Scholl, M.; Ding, S.; Lee, C. W.; Grubbs, R. H. Org. Lett. 1999, 1, 953-956.
33. Barton, D. H. R.; McCombie, S. W. J. Chem. Soc., Perkin Trans. 1 1975, 1574-1585.
34. (a) Hallsworth, A. S.; Henbest, H. B. J. Chem. Soc. 1957, 4604-4608.
35. (b) Brown, H. C.; Ikegami, S.; Kawakami, J. H. J. Org. Chem. 1970, 35, 3243-3245.
36. (c) Mueller, R. H.; Thompson, M. E.; DiPardo, R. M. J. Org. Chem. 1984, 49, 2217-2231.