Selective synthesis of 1-, and 3-carbomethoxy 2-tetralol stereoisomers by microbial reduction of the corresponding tetralones

Tetrahedron Asymmetry

Volumn 7, Issue 10, 1996, Pages 2983-2996

  Abalain, Cécile ^a   Buisson, Didier ^a   Azerad, Robert ^a  

^a CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

TETRALIN DERIVATIVE;

ARTICLE; BACTERIUM; CHIRALITY; DRUG PURIFICATION; DRUG SYNTHESIS; ENZYME ACTIVITY; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030272176     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/0957-4166(96)00389-8     Document Type: Article

References (66)

1. 1. Deol, B. S.; Ridley, D. D.; Simpson, G. W. Aust. J. Chem. 1976, 29, 2459-2467.
2. 2. Frater, G. Helv.Chim.Acta 1979, 62, 2829-2832.
3. 3. Frater, G.; Müller, U.; Günther, W. Tetrahedron 1984, 40, 1269-1277.
4. 4. Buisson, D.; Azerad, R. Tetrahedron Lett. 1986, 27, 2631-2634.
5. 5. Noyori, R.; Ikeda, T.; Okhuma, T.; Widhalm, M.; Kitamura, M.; Takaya, H.; Akutagawa, S.; Sayo, N.; Saito, T.; Taketomi, T.; Kumobayashi, H. J. Am. Chem. Soc. 1989, 111, 9134-9135.
6. 6. Genêt, J. P.; Mallart, S.; Jugé, S., 1989, Fr. Patent n°89 11159; C. A., 1991, 115, 100300j.
7. 6. Genêt, J. P.; Mallart, S.; Jugé, S., 1989, Fr. Patent n°89 11159; C. A., 1991, 115, 100300j.
8. 7. Kitamura, M.; Ohkuma, T.; Tokunaga, M.; Noyori, R. Tetrahedron: Asymmetry 1990, 1, 1-4.
9. 8. Genêt, J. P.; Pinel, C.; Mallart, S.; Jugé, S.; Thorimbert, S.; Laffitte, J.-A. Tetrahedron: Asymmetry 1991, 2, 555-567.
10. 9. Kitamura, M.; Tokunaga, M.; Noyori, R. J. Am. Chem. Soc. 1993, 115, 144-152.
11. 10. Kitamura, M.; Tokunaga, M.; Noyori, R. Tetrahedron 1993, 49, 1853-1860.
12. 11. Genêt, J. P.; Pfister, X.; Ratovelomanana-Vidal, V.; Pinel, C.; Laffitte, J. A. Tetrahedron Lett. 1994, 35, 4559-4562.
13. 12. Genêt, J. P.; Cano De Andrade, M. C.; Ratovelomanana-Vidal, V. Tetrahedron Lett. 1995, 36, 2063-2066.
14. 13. For recent reviews on baker's yeast-mediated reductions, see a) Servi, S. Synthesis 1990, 1-25
15. b) Csuk, R.; Glänzer, B. I. Chem. Rev. 1991, 91, 49-97.
16. 14. Hoffmann, R. W.; Heibig, W.; Ladner, W. Tetrahedron Lett. 1982, 23, 3479-3482.
17. 15. Kitahara, T.; Mori, K. Tetrahedron Lett. 1985, 26, 451-452.
18. 16. Mori, K.; Tsuji, M. Tetrahedron 1986, 42, 435-444.
19. 17. Brooks, D. W.; Wilson, M.; Webb, M. J. Org. Chem. 1987, 52, 2244-2248.
20. 18. Seebach, D.; Roggo, S.; Maetzke, T.; Braunschweiger, H.; Cercus, J.; Krieger, M. Helv. Chem. Acta 1987, 70, 1605-1615.
21. 19. Sato, T.; Maeno, H.; Noro, T.; Fujisawa, T. Chem. Lett. 1988, 1739-1742.
22. 20. Prater, G.; Günter, W.; Müller, U. Helv. Chim. Acta 1989, 72, 1846-1851.
23. 21. Knight, D. W.; Lewis, N.; Share, A. C.; Haigh, D. Tetrahedron-Asymmetry 1993, 4, 625-628.
24. 22. Cooper, J.; Gallagher, P. T.; Knight, D. W. J. Chem. Soc. Perkin Trans. 1 1993, 1313-1317.
25. 23. Ghosh, A. K.; Thompson, W. J.; Munson, P. M.; Liu, W.; Huff, J. Bioorg. Med. Chem. Lett. 1995, 5, 83-88.
26. 24. Toyooka, N.; Yoshida, Y.; Momose, T. Tetrahedron Lett. 1995, 36, 3715-3718.
27. 25. Crisp, G. T.; Meyer, A. G. Tetrahedron 1995, 51, 5831-5846.
28. 26. Hoffmann, R. W.; Ladner, W.; Steinbach, K.; Massa, W.; Schmidt, R.; Snatzke, G. Chem.Ber. 1981, 114, 2786-2801.
29. 27. Akita, H.; Furuichi, A.; Koshiji, H.; Horikoshi, K.; Oishi, T. Chem.Pharm.Bull 1983, 31, 4376-4383.
30. 28. Fujisawa, T.; Itoh, T.; Sato, T. Tetrahedron Lett. 1984, 25, 5083-5086.
31. 29. Akita, H.; Matsukura, H.; Oishi, T. Tetrahedron Lett. 1986, 27, 5397-5400.
32. 30. Nakamura, K.; Miyai, T.; Nozaki, K.; Ushio, K.; Oka, S.; Ohno, A. Tetrahedron Lett. 1986, 27, 3155-3156.
33. 31. Sato, T.; Tsurumaki, M.; Fujisawa, T. Chem.Lett. 1986, 1367-1370.
34. 32. Soukup, M.; Wipf, B.; Hochuli, E.; Leuenberger, H. G. W. Helv.Chim.Acta 1987, 70, 232-236.
35. 33. Buisson, D.; Sanner, C.; Larchevêque, M.; Azerad, R. Tetrahedron Lett. 1987, 28, 3939-3940.
36. 34. Watabu, H.; Ohkubo, M.; Matsubara, H.; Sakai, T.; Tsuboi, S.; Utaka, M. Chem. Lett.1989, 2183-2184.
37. 35. Buisson, D.; Azerad, R.; Sanner, C.; Larchevêque, M. Biocatalysis 1990, 3, 85-93.
38. 36. Nakamura, K.; Miyai, T.; Kawai, Y.; Nakajima, N.; Ohno, A. Tetrahedron Lett. 1990, 31, 1159-1160.
39. 37. Cabon, O.; Larchevêque, M.; Buisson, D.; Azerad, R. Tetrahedron Lett. 1992, 33, 7337-7340.
40. 38. Nakamura, K. In Microbial Reagents in Organic Synthesis (NATO ASI Series C, vol. 381) Servi, S. Ed; Kluwer Academic Publ.: Dordrecht, 1992; pp. 1159-1160.
41. 39. Vanmiddlesworth, F.; Sih, C. J. Biocatalysis 1987, 1, 117-127.
42. 40. Nakamura, K.; Miyai, T.; Nagar, A.; Oka, S.; Ohno, A. Bull. Chem. Soc. Jpn. 1989, 62, 1179-1187.
43. 41. Azerad, R.; Buisson, D. In Microbial Reagents in Organic Synthesis (NATO ASi Series C, vol. 381), Servi, S. Ed; Kluwer Academic Publ.: Dordrecht, 1992; pp. 421-440.
44. 42. Nakamura, K.; Kawai, Y.; Ohno, A. Tetrahedron Lett. 1991, 32, 2927-2928.
45. 43. Kawai, Y.; Kondo, S.; Tsujimoto, M.; Nakamura, K.; Ohno, A. Bull. Chem. Soc. Jpn. 1994, 67, 2244-2247.
46. 44. Nakamura, K.; Kawai, Y.; Miyai, T.; Ohno, A. Tetrahedron Lett. 1990, 31, 3631-3632.
47. 45. Nakamura, K.; Takano, S.; Ohno, A. Tetrahedron Lett 1993, 34, 6087-6090.
48. 46. North, M. Tetrahedron Lett. 1996, 37, 1699-1702.
49. 47. Shieh, W.-R.; Gopalan, A. S.; Sih, C. J. J. Am. Chem. Soc. 1985, 107, 2993-2994.
50. 48. Furuichi, A.; Akita, H.; Matsukura, H.; Oishi, T.; Horikoshi, K. Agric. Biol. Chem. 1985, 49, 2563-2570.
51. 49. Heidlas, J.; Tressl, R. Eur. J. Biochem. 1990, 188, 165-174.
52. 50. Nakamura, K.; Kawai, Y.; Miyai, T.; Honda, S.; Nakajima, N.; Ohno, A. Bull. Chem. Soc. Jpn. 1991, 64, 1467-1470.
53. 51. Peters, J.; Zelinski, T.; Kula, M.-R. Appl.Microbiol.Biotechnol. 1992, 38, 334-340.
54. 52. Nakajima, N.; Ishihara, K.; Kondo, S.; Tsuboi, S.; Utaka, M.; Nakamura, K. Biosc. Biotech. Biochem. 1994, 58, 2080-2081.
55. 53. Buisson, D.; Cecchi, R.; Laffitte, J.-A.; Guzzi, U.; Azerad, R. Tetrahedron Lett. 1994, 35, 3091-3094.
56. 54. Hong, Y.; Gao, Y.; Nie, X.; Zepp, C. M. Tetrahedron Lett. 1994, 35, 6631-6634.
57. 55. Senanayake, C. H.; DiMichele, L. M.; Liu, J.; Fredenburgh, L. E.; Ryan, K. M.; Roberts, F. E.; Larsen, R. D.; Verhoeven, T. R.; Reider, P. J. Tetrahedron Lett. 1995, 36, 7615-7618.
58. 56. Davies, I. W.; Senanayake, C. H.; Castonguay, L.; Larsen, R. D.; Verhoeven, T. R.; Reider, P. J. Tetrahedron Lett. 1995, 36, 7619-7622.
59. 57. Sudo, A.; Saigo, K. Tetrahedron: Asymmetry 1995, 6, 2153-2156.
60. 58. Vebrel, J.; Carrie, R. Bull. Soc. Chim. Fr. 1982, 5-6, 161-166.
61. 59. Pelletier, S. W.; Chappell, R. L.; Parthasarathy, P. C.; Lewin, N. J. Org. Chem. 1966, 31, 1747-1752.
62. 60. Kanerva, L. T.; Sundholm, O. Acta Chem Scand 1993, 47, 823-825.
63. 61. The coordinates, bond distances and angles of 9 are deposited at the Cambridge Crystallographic Data Centre, 12 Union Road, CB2 1EZ, Cambridge, UK.
64. 62. Prelog, V. Pure Appl. Chem. 1964, 9, 119-130.
65. 63. As an additional indication, 1-indanone-2-carboxyesters, in which the carboxyester group cannot adopt a fully axial disposition, are very slowly reduced, affording small amounts of the corresponding cis-hydroxyesters (D. Buisson, J.A.Laffitte and R. Azerad, unpublished results).
66. 64. Gilbert, J. C.; Selliah, R. D. J. Org. Chem. 1993, 58, 6255-6265.