A general and stereoselective approach to nonactate esters and isomers: A versatile synthesis of (+)-methyl nonactate

Tetrahedron

Volumn 53, Issue 50, 1997, Pages 17079-17088

  Mandville, Gérard ^a   Girard, Christian ^a   Bloch, Robert ^a  

^a UNIVERSITÉ PARIS SUD   (France)

Author keywords

[No Author keywords available]

Indexed keywords

NONACTIC ACID METHYL ESTER; TETRAHYDROFURAN DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; IN VITRO STUDY; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030780835     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)10118-1     Document Type: Article

References (42)

1. a) Corbaz, R.; Ettlinger, L.; Gaumann, F.; Keller-Schierlein, W.; Kradolfer, F.; Neipp; L.; Prelog, V.; Zähner, H. Helv. Chim. Acta 1955, 38, 1445-1448.
2. b) Dominguez, J.; Dunitz, J.D.; Gerlach, H.; Prelog, V. Helv. Chim. Acta 1962, 45, 129-128.
3. c) Gerlach, H.; Prelog, V. Liebigs Ann. Chem. 1963, 669, 121-135.
4. a) For a review of the syntheses reported before 1987 see: Lygo, B. Tetrahedron 1988,44, 6889-6896.
5. b) Warm, A.; Vogel, P. Helv. Chim. Acta 1987, 70, 690-700.
6. c) Walkup, R.D.; Park, G. J. Am. Chem. Soc. 1990, 112, 1597-1603;
7. d) Deschenaux, P.F.; Jacot-Gillarmod, A. Helv. Chim. Acta 1990, 73, 1861.
8. e) Yqbal, J.; Pandey, A.; Chauman, B.P.S. Tetrahedron 1991, 47, 4143-4154.
9. f) Kim, B.H.; Lee, J.Y. Tetrahedron Lett. 1992, 33, 2557-2560.
10. g) Honda, T.; Ishige, H.; Araki, J.; Akimoto, S.; Hirayama, K.; Tsubuki, M. Tetrahedron 1992, 48, 79-88.
11. h) Kim, B.H.; Lee, J.Y. Tetrahedron Lett. 1993, 34, 1609-1610.
12. i) Takatori, K.; Tanaka, N.; Tanaka, K.; Kajiwara, M. Heterocycles 1993, 36, 1489-1492.
13. j) Solladie, G.; Dominguez, C. J. Org. Chem. 1994, 59, 3898-3901.
14. k) Fleming, I.; Ghosh, S.K. J. Chem. Soc. Chem. Commun. 1994, 2285-2288.
15. l) Lee, J.Y.; Kim, B.H. Tetrahedron Lett. 1995, 36, 3361-3364.
16. m) Lee, J.Y.; Kim, B.H. Tetrahedron 1996, 52, 571-588.
17. n) Metz, P.; Meiners, U.; Cramer, E.; Fröhlich, R.; Wibbeling, B. J. Chem. Soc. Chem. Commun. 1996, 431-432.
18. o) Bratt, K.; Garavelas, A.; Perlmutter, P.; Nestman, G. J. Org. Chem. 1996, 61, 2109-2117.
19. p) Abe, M.; Kiyota, H.; Adachi, M.; Oritani, T. Synlett 1996, 777-778.
20. For reviews see: a) Harmange, J.C.; Figadere, B. Tetrahedron: Asymmetry 1993, 4, 1711-1754.
21. b) Cardillo, G.; Orena, M. Tetrahedron 1990, 46, 3321-3408.
22. c) Boivin, T.L. Tetrahedron 1987, 43, 3309-3362.
23. a) Gerlach, H.; Wetter, H. Helv. Chim. Acta 1974, 57, 2306-2321.
24. b) Ohrui, H.; Jones, C.H.; Moffatt, J.G.; Maddox, M.L.; Christensen, A.T.; Byram, S.K. J. Am. Chem. Soc. 1975, 97, 4602-4613.
25. c) Ohrui, H.; Emoto, S. J. Org. Chem. 1917, 42, 1951-1957.
26. d) Kane, P.D.; Mann, J. J. Chem. Soc. Chem. Commun. 1983, 224-226.
27. e) Ko, S.S.; Klein, L.L.; Pfaff, K.P.; Kishi, Y. Tetrahedron Lett. 1982, 23, 4415-4418.
28. f) Maryanoff, B.E.; Nortey, S.O.; Inners, R.R.; Campbell, S.A.; Reitz, A.B.; Liotta, D. Carbohydrates Res. 1987, 777, 259-278.
29. g) Reitz, A.B.; Jordan Jr, A.D.; Maryanoff, B.E. J. Org. Chem. 1987, 52, 4800-4802.
30. h) Baldwin, J.E.; Adlington, R.M.; Robinson, N.G. Tetrahedron Lett. 1988, 29, 375-378.
31. i) Lee, H.W. Tetrahedron Lett. 1990, 31, 7637-7640.
32. j) Marot, C.; Rollin, P. Tetrahedron Lett. 1994, 35, 8377-8380.
33. Girard, C.; Mandville, G.; Shi, H.; Bloch, R. Tetrahedron Lett. 1996, 37, 63-64.
34. Cinquin, C.; Shaper, I.; Mandville, G.; Bloch, R. Synlett 1995, 339-340.
35. Bloch, R.; Gilbert, L. J. Org. Chem. 1987, 52, 4603-4605.
36. Evans, D.A.; Chapman, K.T.; Carreira, E.M. J. Am. Chem. Soc. 1988, 110, 3560-3578.
37. a) Rychnovsky, S.D.; Skalitzky, D.J. Tetrahedron Lett. 1990, 31, 945-948.
38. b) Evans, D.A.; Rieger, D.L.; Gage, J.R. Tetrahedron Lett. 1990, 31, 7099-7100.
39. c) Rychnovsky, S.D.; Rogers. B.; Yang, G. J. Org. Chem. 1993, 58, 3511-3515.
40. Mori, Y.; Kuhara, M.; Takeuchi, A.; Suzuki, M. Tetrahedron Lett. 1988, 29, 5419-5422 and references therein.
41. Ando, K. Tetrahedron Lett. 1995, 36, 4105-4108.
42. Etemad-Moghadam, G.; Seyden-Penne, J. Tetrahedron 1984, 40, 5153-5166 and references cited therein.