Synthesis of enantiomerically pure bicyclic condensed δ-lactones via microbial reduction and enzymic resolution strategies

Tetrahedron Asymmetry

Volumn 11, Issue 12, 2000, Pages 2599-2614

  Fogal, Erica ^a   Forzato, Cristina ^a   Nitti, Patrizia ^a   Pitacco, Giuliana ^a   Valentin, Ennio ^a  

^a UNIVERSITY OF TRIESTE   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ALICYCLIC COMPOUND; LACTONE; LACTONE DERIVATIVE; OXOACID;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL STRUCTURE; CIRCULAR DICHROISM; CONFORMATION; CONTROLLED STUDY; DIASTEREOISOMER; ENANTIOMER; INFRARED SPECTROSCOPY; MASS SPECTROMETRY; POLYMERIZATION; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; REDUCTION; SACCHAROMYCES CEREVISIAE; STEREOCHEMISTRY; SYNTHESIS;

EID: 0034733523     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(00)00218-4     Document Type: Article

References (71)

1. (a) Sih, C. J.; Rosazza, J. P. In Applications of Biochemical Systems in Organic Chemistry; Sih, C. J., Ed.; John Wiley & Sons: New York, 1976, Part I, Chapter III
2. (b) Kieslih, K. Microbial Transformations of non-Steroid Cyclic Compounds; George Thieme: Stuttgart, 1976
3. (c) Fischli, A. In Modern Synthetic Methods; Sheffold, S., Ed.; Salle-Sauerländer: Frankfurt, 1980
4. (d) Sih, C. J.; Chen, C.-S. Angew. Chem., Int. Ed. Engl. 1984, 23, 570-578
5. (e) Jones, B. Tetrahedron 1986, 42, 3351-3403
6. (f) Yamada, H.; Shimizu, S. Angew. Chem., Int. Ed. Engl. 1988, 27, 622-642
7. (g) Chen, C.-S.; Sih, C. J. Angew. Chem., Int. Ed. Engl. 1989, 28, 695-707
8. (h) Santaniello, E.; Ferraboschi, P.; Grisenti, P.; Manzocchi, A. Chem. Rev. 1992, 92, 1071-1140
9. (i) Microbial Reagents in Organic Synthesis; Servi, S., Ed.; Kluwer Academic Publisher: Dordrecht, 1992
10. (j) Preparative Biotransformations: Whole Cells and Isolated Enzymes in Organic Chemistry, Roberts, S. M.; Wiggins, K.; Cases, G., Eds.; John Wiley & Sons: Chichester, 1993
11. (k) Wong, C. H.; Whitesides, G. M. Enzymes in Synthetic Organic Chemistry; Elsevier Science: Oxford, 1994
12. (l) Faber, K. Biotransformations in Organic Chemistry; Springer-Verlag; Berlin, 1997.
13. (a) Servi, S. Synthesis 1990, 1-25
14. (b) Csuk, R.; Glänzer, B. I. Chem. Rev. 1991, 91, 49-97.
15. Kawai, Y.; Kondo, S.; Tsujimoto, M.; Nakamura, K.; Ohno, A. Bull. Chem. Soc. Jpn. 1994, 67, 2244-2247.
16. (a) Russell, A. J.; Klibanov, A. M. J. Biol. Chem. 1988, 263, 11624-11626
17. (b) Ushio, K.; Hada, J.; Tanaka, Y.; Ebara, K. Enzyme Microb. Technol. 1993, 15, 222-228
18. (c) Dao, D. H.; Kawai, Y.; Hida, K.; Hornes, S.; Nakamura, K.; Ohno, A.; Okamura, M.; Akasaka, T. Bull. Chem. Soc. Jpn. 1998, 71, 425-432.
19. (a) North, M. Tetrahedron Lett. 1996, 37, 1699-1702
20. (b) Rotthaus, O.; Kruger, D.; Demuth, M.; Shafner, K. Tetrahedron 1997, 53, 935-938.
21. (a) Nakamura, K.; Higaki, M.; Ushio, K.; Oka, S.; Ohno, A. Tetrahedron Lett. 1985, 26, 4213-4216
22. (b) Naoshima, Y.; Hasegawa, H. Chem. Lett 1987, 2379-2382
23. (c) Naoshima, Y.; Maeda, J.; Munakata, Y. J. Chem. Soc., Perkin Trans. 1 1992, 659-660, and references cited therein.
24. (a) Kawai, Y.; Hida, K.; Tsujimoto, M.; Kondo, S.; Kitano, K.; Nakamura, K.; Ohno, A. Bull. Chem. Soc. Jpn. 1999, 72, 99-102, and references cited therein
25. (b) Ema, T.; Sugiyama, Y.; Fukumoto, M.; Moriya, H.; Cui, J.-N.; Sakai, T.; Utaka, M. J. Org. Chem. 1998, 63, 4996-5000, and references cited therein.
26. (a) Deol, B. S.; Ridley, D. D.; Simpson, G. W. Aust. J. Chem. 1976, 29, 2459-2467
27. (b) Tsuboi, S.; Nishiyama, E.; Furutani, H.; Takeda, A. J. Org. Chem. 1987, 52, 1359-1362
28. (c) Nakamura, K.; Kondo, S.; Nakajima, N.; Ohno, A. Tetrahedron 1995, 51, 687-694
29. (d) Drioli, S.; Nitti, P.; Pitacco, G.; Tossut, L.; Valentin, E. Tetrahedron: Asymmetry 1999, 10, 2713-2728
30. (e) Ridley, D. D.; Stralow, M. J. Chem. Soc. Chem. Commun. 1975, 400
31. (f) Akita, H.; Furuiki, A.; Koshiji, H.; Horikoshi, K.; Oishi, T. Chem. Pharm. Bull. 1983, 31, 4384-4390.
32. (a) Hirama, M.; Shimizu, M.; Iwashita, M. J. Chem. Soc. Chem. Commun. 1983, 599-600
33. (b) Mori, K.; Mori, H.; Sugai, T. Tetrahedron 1985, 41, 919-925
34. (c) Buisson, D.; Azerad, R. Tetrahedron Lett. 1986, 27, 2631-2634
35. (d) Seebach, D.; Roggo, S.; Maetzke, T.; Braunschweiger, H.; Cercus, J.; Krieger, M. Helv. Chim. Acta 1987, 70, 1605-1615
36. (e) Utaka, M.; Watabu, H.; Higashi, H.; Sakai, T.; Tsuboi, S.; Torii, S. J. Org. Chem. 1990, 55, 3917-3921
37. (f) Ghosh, S. K.; Chattopadhyay, S.; Mamdapur, V. R. Tetrahedron 1991, 47, 3089-3094
38. (g) Hayakawa, R.; Nozawa, K.; Shimizu, M.; Fujisawa, T. Tetrahedron Lett. 1998, 39, 67-70.
39. (a) Tuynenburg Muys, G.; van der Ven, B.; de Jonge, A. P. Nature 1962, 194, 995-996
40. (b) Utaka, M.; Watabu, H.; Takeda, A. J. Org. Chem. 1987, 52, 4363-4368
41. (c) Manzocchi, A.; Casati, R.; Fiecchi, A.; Santaniello, E. J. Chem. Soc., Perkin Trans. 1 1987, 2753-2757
42. (d) Moriuchi, F.; Muroi, H.; Aibe, H. Chem. Lett. 1987, 1141-1144
43. (e) Fujisawa, T.; Mobele, B. I.; Shimizu, M. Tetrahedron Lett. 1991, 32, 7055-7058
44. (f) Tsuboi, S.; Sakamoto, J.; Kawano, T.; Utaka, M.; Takeda, A. J. Org. Chem. 1991, 56, 7177-7179
45. (g) Aquino, M.; Cardani, S.; Fronza, G.; Fuganti, C.; Fernandez, R. P.; Tagliani, A. Tetrahedron 1991, 47, 7887-7896
46. (h) Fantin, G.; Fagagnolo, M.; Medici, A.; Pedrini, P.; Poli, S. Tetrahedron: Asymmetry 1992, 3, 107-114
47. (i) Taylor, S. K.; Atkinson, R. F.; Almli, E. P.; Carr, M. D.; Van Huis, T. J.; Whittakar, M. R. Tetrahedron: Asymmetry 1995, 6, 157-164.
48. (a) Francke, A. Biochem. J. 1965, 95, 633-640
49. (b) Han, C.-Q.; Di Tullio, D.; Wang, Yi-F.; Sih, C. J. J. Org. Chem. 1986, 51, 1253-1258
50. (c) Fronza, G.; Fuganti, C.; Grasselli, P.; Terreni, M. Tetrahedron 1992, 48, 7363-7372.
51. Blanco, L.; Guibé-Jampel, E.; Rousseau, G. Tetrahedron Lett. 1988, 29, 1915-1918.
52. (a) Goergens, U.; Schneider, M. P. Tetrahedron: Asymmetry 1992, 3, 831-832
53. (b) Haase, B.; Schneider, M. P. Tetrahedron: Asymmetry 1993, 4, 1017-1026.
54. Forzato, C.; Nitti, P.; Pitacco, G.; Valentin, E. Tetrahedron: Asymmetry 1999, 10, 1243-1254.
55. Stork, G.; Brizzolara, A.; Landesman, H.; Szmuszkovicz, J.; Terrel, R. J. Am. Chem. Soc. 1963, 85, 207-222.
56. Ghera, E.; Yechezkel, T.; Hassner, A. J. Org. Chem. 1990, 55, 5977-5982.
57. Ando, K.; Condroski, K. R.; Houk, K. N.; Wu, Y.-D.; Ly, S. K.; Overman, L. E. J. Org. Chem. 1998, 63, 3196-3203.
58. Günther, C.; Mosandl, A. Liebigs Ann. Chem. 1986, 2112-2122.
59. (a) Krishnamurthy, S.; Brown, H. C. J. Am. Chem. Soc. 1972, 94, 7159-7161
60. (b) Podraza, K. F. J. Heterocyclic Chem. 1987, 24, 293-298.
61. Lunazzi, L.; Casarini, D.; Anderson, J. E. Gazz. Chim. Ital. 1990, 120, 217-221.
62. (a) Marshall, H.; Penninger, J.; Weyerstahl, P.; Liebigs Ann. Chem. 1982, 49-67
63. (b) von Plattner, A.; Fürst, A.; Jirasek, K. Helv. Chim. Acta 1946, 29, 730-739.
64. Green, S. P.; Whiting, D. A. J. Chem. Soc., Perkin Trans 1, 1996, 1027-1034.
65. Edward, J.; Cooke, E.; Paradellis, T. C. Can. J. Chem. 1981, 59, 597-600.
66. Bestmann, H. J.; Schade, G.; Lutke, H.; Monius, Th. Chem. Ber. 1985, 118, 2640-2658.
67. (a) Gutsche, C. D.; Tao, I. Y. C. J. Org. Chem., 1967, 32, 1778-1781
68. (b) Jacob, T. M.; Vatakencherry, P. A.; Dev, S. Tetrahedron 1964, 20, 2815-2820.
69. Mabic, S.; Castagnoli, N. J. Org. Chem. 1996, 61, 309-313.
70. Krishnamurthy, S.; Brown, H. C. J. Am. Chem. Soc. 1976, 98, 3383-3384.
71. MacCorquodale, F.; Walton, J. C. J. Chem. Soc. Perkin Trans. 1 1989, 347-352.