Asymmetric synthesis of (S)-2,6-dimethylchroman-4-one

Arkivoc

Volumn 2001, Issue 11, 2001, Pages 74-79

  Hodgetts, Kevin J ^a,b  

^a UNIVERSITY COLLEGE DUBLIN   (Ireland)

^b NEUROGEN CORPORATION   (United States)

Author keywords

(S) 2,6 dimethylchroman 4 one; Chromanones; Intramolecular Mitsunobu cyclization; Stereocontrolled route

Indexed keywords

2,6 DIMETHYLCHROMAN 4 ONE; CHROMAN DERIVATIVE; PLANT EXTRACT; UNCLASSIFIED DRUG;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; LEONTOPODIUM ALPINUM; MEDICINAL PLANT; MITSUNOBU REACTION;

EID: 3242776229     PISSN: 14246376     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (36)

1. (a) Dean, F.M., Naturally Occurring Oxygen Ring Compounds, Butterworths, London, 1963.
2. (b) Ellis, G.P.; Lockhart, I.M., Chromans and Tocopherols, Wiley, New York, 1977.
3. (c) Saengchantara, S.T.; Wallace, T. W. Nat. Prod. Rep. 1986, 3, 465.
4. (d) Geen, G.; Evans, J. M.; Vong, A. K. Comprehensive Heterocyclic Chemistry II; McKillop, A.; Ed.; Pergamon: Oxford, 1996; Vol. 5, pp. 469.
5. Chandler, I.M.; McIntyre, C.R.; Simpson, T.J. J. Chem. Soc., Perkin Trans. 1 1992, 2271.
6. For examples see: (a) Erdtman, H. Svensk Kem. Tidskr. 1944, 56, 95;
7. (b) Lindstedt, G. Acta Chem. Scand. 1950, 4, 1042;
8. (c) Wollenweber, E. Phytochemistry 1982, 20, 1462;
9. (d) Jaipetch, T.; Reutrakul, V.; Tuntiwachwuttikul, P.; Santisuk, T. Phytochemistry 1983, 22, 625;
10. (e) Haberlein, H.; Tschiersch, K-P. Biochemical Systematics and Ecology 1998, 26, 97.
11. Comey, N.; Hook, I.; Sheridan, H.; Walsh, J.; James, P. J. J. Nat. Prod. 1997, 60, 148.
12. For some recent approaches to vitamin E see: (a) Harada, T.; Hayashiya, T.; Wada, I.; Iwaake, N.; Oku, A. J. Am. Chem. Soc. 1987, 109, 527;
13. (b) Inoue, S.; Ikeda, H.; Sato, S.; Horie, K.; Ota, T.; Miyamoto, O.; Sato, K. J. Org. Chem. 1987, 52, 5495;
14. (c) Hubsher, J.; Barner, R. Helv. Chem. Acta 1990, 73, 1068;
15. (d) Mizuguchi, S.; Suzuki, T.; Achiwa, K. Synlett 1996, 743;
16. (e) Tietze, L.F.; Gorlitzer, J. Synthesis 1997, 877.
17. (a) Saengchantara, S.T.; Wallace, T.W. J. Chem. Soc., Chem. Commun., 1986, 1592;
18. (b) Saengchantara, S.T.; Wallace, T.W. Tetrahedron 1990, 46, 6553.
19. (c) For a recent application to the synthesis of a flavanone, see Solladié, G.; Gehrold, N.; Maigan, J. Tetrahedron: Asymmetry 1999, 10, 2739.
20. Rama Rao, A.V.; Gaitonde, A.S.; Prakash, K.R.C.; Prahlada Rao, S. Tetrahedron Lett. 1994, 35, 6347.
21. (a) Sato, K.; Tomoyuki, Y.; Mitsuru, S.; Shishido, K. J. Org. Chem. 2001, 66, 309;
22. (b) Birkett, M. A.; Knight, D. W.; Little, P. B.; Mitchell, M. B. Tetrahedron 2000, 56, 1013.
23. (a) Wipf, P.; Weiner, W. S. J. Org. Chem. 1999, 64, 5321;
24. (b) Johannes, C. W.; Visser, M. S.; Weatherhead, G. S.; Hoveyda, A. H. J. Am. Chem. Soc. 1998, 120, 8340 and references cited therein.
25. Trost, B. M.; Toste, F. D. J. Am. Chem. Soc. 1998, 120, 9074.
26. (a) Akuamoah, R. K.; Brown, P. E.; Marcus, W. Y.; Steel, J. E. J. Chem. Soc., Perkin Trans. 1 1995, 197;
27. (b) Anastasis, P.; Brown, P. E. J. Chem. Soc., Perkin Trans. 1 1983, 197.
28. (a) Hodgetts, K. J. Tetrahedron Lett. 2000, 41, 8655;
29. (b) Hodgetts, K. J. Tetrahedron Lett. 2001, 42, 3763.
30. Purchased from Aldrich, 99% e.e. by GLC.
31. Nahm, S.; Weinreb, S. M. Tetrahedron Lett. 1981, 22, 3815.
32. Mitsunobu, O. Synthesis 1981, 1.
33. Baldwin, J. E.; Thomas, R. C.; Kruse, L. I.; Silberman, L. J. Org. Chem. 1977, 42, 3846.
34. Hodgetts, K. J.; Maragkou, K. I.; Wallace, T. W.; Wootton, R. C. R. Tetrahedron 2001, 57, 6793.
35. Rautenstrauch, V.; Lindstrom, M.; Bourdin, B.; Currie, J.; Oliveros, E. Helv. Chim. Acta 1993, 76, 607.
36. Ireland, R. E.; Wardle, R. B. J. Org. Chem. 1987, 52, 1780.