Enzymatic asymmetrisation of prochiral α,α-disubstituted-malonates and -1,3-propanediols: Formal asymmetric syntheses of (-)-aphanorphine and (+)-eptazocine

Tetrahedron Asymmetry

Volumn 8, Issue 3, 1997, Pages 371-374

  Fadel, Antoine ^a   Arzel, Philippe ^a  

^a UNIVERSITÉ PARIS SACLAY   (France)

Author keywords

[No Author keywords available]

Indexed keywords

APHANORPHINE; EPTAZOCINE;

ARTICLE; CATALYSIS; CHIRALITY; DRUG SYNTHESIS; PRIORITY JOURNAL; REACTION ANALYSIS;

EID: 0031046483     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(96)00538-1     Document Type: Article

References (31)

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2. (a) Martin, S.F. Tetrahedron 1980, 36, 419;
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4. Fuji, K. Chem. Rev. 1993, 93, 2037 and references cited therein.
5. For (-)-aphanorphine see: (a) Gulavita, N.; Hori, A.; Shimizu, Y.; Laszlo, P.; Clardy, J. Tetrahedron Lett. 1988, 29, 4381;
6. (b) Takano, S.; Inomata, K.; Sato, T.; Ogasawara, K. J Chem. Soc. Chem. Commun. 1989, 1591;
7. (c) Takano, S.; Inomata, K.; Sato, T.; Takahashi, M.; Ogasawara, K. J. Chem. Soc. Chem. Commun. 1990, 290;
8. (d) Takemoto, T.; Sodeoka, M.; Sasai, H.; Shibasaki, M. J. Am. Chem. Soc. 1993, 115, 8477 and see corrections ibid J. Am. Chem. Soc. 1994, 116, 11207;
9. (d) Takemoto, T.; Sodeoka, M.; Sasai, H.; Shibasaki, M. J. Am. Chem. Soc. 1993, 115, 8477 and see corrections ibid J. Am. Chem. Soc. 1994, 116, 11207;
10. (e) Hulme, A.N.; Henry, S.S.; Meyers, A.I. J. Org. Chem. 1995, 60, 1265;
11. (f) Node, M.; Imazato, H.; Kurosaki, R.; Kawano, Y.; Inoue, T.; Nishide, K. Heterocycles 1996, 42, 811 and references cited therein.
12. For eptazocine see: (a) Shiotani, S.; Kometani, T. Chem. Pharm. Bull. 1973, 27, 1053;
13. (b) Shiotani, T.; Kometani, K.; Nozawa, T.; Kurobe, A.; Futsukaichi, O. J. Med. Chem. 1979, 22, 1558 and references cited therein;
14. (c) ref. 3(f);
15. (d) ref. 3(d);
16. (e) Shiotani, S.; Okada, H.; Yamamoto, T.; Nakamata, K.; Adachi, J.; Nakamoto, H. Heterocycles 1996, 43, 113 and references cited therein.
17. (a) Fadel, A.; Garcia-Argote, S. Tetrahedron: Asymmetry 1996, 7, 1159;
18. (b) Fadel, A.; Canet, J.L.; Salaün, J. Tetrahedron: Asymmetry 1993, 4, 27;
19. (c) Canet, J.-L.; Fadel, A.; Salaün, J. J. Org. Chem. 1992, 57, 3463 and references cited therein.
20. Fadel, A.; Arzel, Ph. Tetrahedron: Asymmetry 1995, 6, 893.
21. Mancuso, A.J.; Huang, S.L.; Swern, D. J. Org. Chem. 1978, 43, 2480.
22. Blanchette, M.A.; Choy, S.; Davis, J.T.; Essenfeld, A.P.; Masamune, S.; Roush, W.R.; Sakai, T. Tetrahedron Lett. 1984, 25, 2183.
23. Brown, H.C.; Brown, C.A. J. Am. Chem. Soc. 1963, 85, 1003.
24. 4: C, 74.12; H, 7.92. Found: C, 73.92; H, 7.72.
25. 2: C, 81.59; H, 7.54. Found: C, 81.47; H, 7.49.
26. 2: C, 75.68; H, 8.80. Found: C, 75.67; H, 8.83.
27. Bowden, K.; Heilbron, I.M.; Jones, E.R.H.; Weedon, B.C.L. J. Chem, Soc. 1946, 39.
28. 3) δ 196.8 (s), 180.8 (s), [6 arom.C, 163.9 (s), 146.8 (s), 130.1 (d), 125.3 (s), 113.1 (d), 112.7 (d)], 55.5 (q), 45.9 (s), 34.9 (t), 33.7 (t), 25.7 (q).
29. Very recently, the corresponding malonate was used to prepare the chiral acid ester according to ref. 5(c),6 by enzymatic hydrolysis with PLE, see: Hallinan, K.O.; Honda, T. Tetrahedron 1995, 51, 12211.
30. 4-DMSO) did not improve the yield.
31. 3).