Simple methods for the preparation of enantiomerically pure abscisic acid (ABA) analogues from (S)-(+)-ABA

Synthetic Communications

Volumn 27, Issue 12, 1997, Pages 2133-2142

  Ward, Dale E ^a   Gai, Yuanzhu ^a  

^a UNIVERSITY OF SASKATCHEWAN   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ABSCISIC ACID; ALDEHYDE; OXALYL CHLORIDE; REAGENT; UNCLASSIFIED DRUG;

ARTICLE; COST; ENANTIOMER; HORMONE SYNTHESIS; REACTION ANALYSIS; SYNTHESIS;

EID: 0031006120     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1080/00397919708006821     Document Type: Article

References (39)

1. Abscisic Acid; Addicott, F. T., Ed.; Praeger: New York, 1983.
2. Abscisic Acid: Physiology and Biochemistry; Davies, W. J.; Jones, H. G., Eds; BIOS Scientific: Oxford, 1991.
3. For (±)-ABA: (a) Cornforth, J. W.; Milborrow, B. V.; Ryback, G. Nature 1965, 206, 715. (b) Cornforth, J. W.; Mallaby, R.; Ryback, G. J. Chem. Soc. C 1968, 1565-1568. (c) Roberts, D. L.; Heckman, R. A.; Hege, B. P.; Bellin, S. A. J. Org. Chem. 1968, 33, 3566-3569. (d) Findlay, J. A.; MacKay, W. D. Can. J. Chem. 1971, 49, 2369-2371. (e) Mayer, H. J.; Rigassi, N.; Schwieter, U.; Weedon, B. C. L. Helv. Chim. Acta 1976, 59, 1424-1427. (f) Constantino, M. G.; Losco, P.; Castellano, E. E. J. Org. Chem. 1989, 54, 681-683.
4. For (±)-ABA: (a) Cornforth, J. W.; Milborrow, B. V.; Ryback, G. Nature 1965, 206, 715. (b) Cornforth, J. W.; Mallaby, R.; Ryback, G. J. Chem. Soc. C 1968, 1565-1568. (c) Roberts, D. L.; Heckman, R. A.; Hege, B. P.; Bellin, S. A. J. Org. Chem. 1968, 33, 3566-3569. (d) Findlay, J. A.; MacKay, W. D. Can. J. Chem. 1971, 49, 2369-2371. (e) Mayer, H. J.; Rigassi, N.; Schwieter, U.; Weedon, B. C. L. Helv. Chim. Acta 1976, 59, 1424-1427. (f) Constantino, M. G.; Losco, P.; Castellano, E. E. J. Org. Chem. 1989, 54, 681-683.
5. For (±)-ABA: (a) Cornforth, J. W.; Milborrow, B. V.; Ryback, G. Nature 1965, 206, 715. (b) Cornforth, J. W.; Mallaby, R.; Ryback, G. J. Chem. Soc. C 1968, 1565-1568. (c) Roberts, D. L.; Heckman, R. A.; Hege, B. P.; Bellin, S. A. J. Org. Chem. 1968, 33, 3566-3569. (d) Findlay, J. A.; MacKay, W. D. Can. J. Chem. 1971, 49, 2369-2371. (e) Mayer, H. J.; Rigassi, N.; Schwieter, U.; Weedon, B. C. L. Helv. Chim. Acta 1976, 59, 1424-1427. (f) Constantino, M. G.; Losco, P.; Castellano, E. E. J. Org. Chem. 1989, 54, 681-683.
6. For (±)-ABA: (a) Cornforth, J. W.; Milborrow, B. V.; Ryback, G. Nature 1965, 206, 715. (b) Cornforth, J. W.; Mallaby, R.; Ryback, G. J. Chem. Soc. C 1968, 1565-1568. (c) Roberts, D. L.; Heckman, R. A.; Hege, B. P.; Bellin, S. A. J. Org. Chem. 1968, 33, 3566-3569. (d) Findlay, J. A.; MacKay, W. D. Can. J. Chem. 1971, 49, 2369-2371. (e) Mayer, H. J.; Rigassi, N.; Schwieter, U.; Weedon, B. C. L. Helv. Chim. Acta 1976, 59, 1424-1427. (f) Constantino, M. G.; Losco, P.; Castellano, E. E. J. Org. Chem. 1989, 54, 681-683.
7. For (±)-ABA: (a) Cornforth, J. W.; Milborrow, B. V.; Ryback, G. Nature 1965, 206, 715. (b) Cornforth, J. W.; Mallaby, R.; Ryback, G. J. Chem. Soc. C 1968, 1565-1568. (c) Roberts, D. L.; Heckman, R. A.; Hege, B. P.; Bellin, S. A. J. Org. Chem. 1968, 33, 3566-3569. (d) Findlay, J. A.; MacKay, W. D. Can. J. Chem. 1971, 49, 2369-2371. (e) Mayer, H. J.; Rigassi, N.; Schwieter, U.; Weedon, B. C. L. Helv. Chim. Acta 1976, 59, 1424-1427. (f) Constantino, M. G.; Losco, P.; Castellano, E. E. J. Org. Chem. 1989, 54, 681-683.
8. For (±)-ABA: (a) Cornforth, J. W.; Milborrow, B. V.; Ryback, G. Nature 1965, 206, 715. (b) Cornforth, J. W.; Mallaby, R.; Ryback, G. J. Chem. Soc. C 1968, 1565-1568. (c) Roberts, D. L.; Heckman, R. A.; Hege, B. P.; Bellin, S. A. J. Org. Chem. 1968, 33, 3566-3569. (d) Findlay, J. A.; MacKay, W. D. Can. J. Chem. 1971, 49, 2369-2371. (e) Mayer, H. J.; Rigassi, N.; Schwieter, U.; Weedon, B. C. L. Helv. Chim. Acta 1976, 59, 1424-1427. (f) Constantino, M. G.; Losco, P.; Castellano, E. E. J. Org. Chem. 1989, 54, 681-683.
9. For (S)-(+)-ABA: (a) Oritani, T.; Yamashita, K. Tetrahedron Lett. 1972, 2521-2524. (b) Mori, K. Tetrahedron 1973, 30, 1065-1072. (c) Galbraith, M. N.; Horn, D. H. S. J. Chem. Soc., Chem. Commun. 1973, 566-567. (d) Shibisaki, M.; Terashima, S.; Yamada, S. Chem. Pharm. Bull. 1976, 24, 315-322. (e) Kienzle, F.; Mayer, H.; Minder, R. E.; Thommen, H. Helv. Chim. Acta 1978, 61, 2616-2627. (f) Acemonglu, M.; Uebelhart, P.; Rey, M.; Eugster, C. H. Helv. Chim. Acta 1988, 71, 931-955. (g) Soukup, M.; Lukac, T.; Lohri, B.; Widmer, E. Helv. Chim. Acta 1989, 72, 361-364. (h) Sakai, K.; Takahashi, K.; Nukano, T. Tetrahedron 1992, 48, 8229-8238.
10. For (S)-(+)-ABA: (a) Oritani, T.; Yamashita, K. Tetrahedron Lett. 1972, 2521-2524. (b) Mori, K. Tetrahedron 1973, 30, 1065-1072. (c) Galbraith, M. N.; Horn, D. H. S. J. Chem. Soc., Chem. Commun. 1973, 566-567. (d) Shibisaki, M.; Terashima, S.; Yamada, S. Chem. Pharm. Bull. 1976, 24, 315-322. (e) Kienzle, F.; Mayer, H.; Minder, R. E.; Thommen, H. Helv. Chim. Acta 1978, 61, 2616-2627. (f) Acemonglu, M.; Uebelhart, P.; Rey, M.; Eugster, C. H. Helv. Chim. Acta 1988, 71, 931-955. (g) Soukup, M.; Lukac, T.; Lohri, B.; Widmer, E. Helv. Chim. Acta 1989, 72, 361-364. (h) Sakai, K.; Takahashi, K.; Nukano, T. Tetrahedron 1992, 48, 8229-8238.
11. For (S)-(+)-ABA: (a) Oritani, T.; Yamashita, K. Tetrahedron Lett. 1972, 2521-2524. (b) Mori, K. Tetrahedron 1973, 30, 1065-1072. (c) Galbraith, M. N.; Horn, D. H. S. J. Chem. Soc., Chem. Commun. 1973, 566-567. (d) Shibisaki, M.; Terashima, S.; Yamada, S. Chem. Pharm. Bull. 1976, 24, 315-322. (e) Kienzle, F.; Mayer, H.; Minder, R. E.; Thommen, H. Helv. Chim. Acta 1978, 61, 2616-2627. (f) Acemonglu, M.; Uebelhart, P.; Rey, M.; Eugster, C. H. Helv. Chim. Acta 1988, 71, 931-955. (g) Soukup, M.; Lukac, T.; Lohri, B.; Widmer, E. Helv. Chim. Acta 1989, 72, 361-364. (h) Sakai, K.; Takahashi, K.; Nukano, T. Tetrahedron 1992, 48, 8229-8238.
12. For (S)-(+)-ABA: (a) Oritani, T.; Yamashita, K. Tetrahedron Lett. 1972, 2521-2524. (b) Mori, K. Tetrahedron 1973, 30, 1065-1072. (c) Galbraith, M. N.; Horn, D. H. S. J. Chem. Soc., Chem. Commun. 1973, 566-567. (d) Shibisaki, M.; Terashima, S.; Yamada, S. Chem. Pharm. Bull. 1976, 24, 315-322. (e) Kienzle, F.; Mayer, H.; Minder, R. E.; Thommen, H. Helv. Chim. Acta 1978, 61, 2616-2627. (f) Acemonglu, M.; Uebelhart, P.; Rey, M.; Eugster, C. H. Helv. Chim. Acta 1988, 71, 931-955. (g) Soukup, M.; Lukac, T.; Lohri, B.; Widmer, E. Helv. Chim. Acta 1989, 72, 361-364. (h) Sakai, K.; Takahashi, K.; Nukano, T. Tetrahedron 1992, 48, 8229-8238.
13. For (S)-(+)-ABA: (a) Oritani, T.; Yamashita, K. Tetrahedron Lett. 1972, 2521-2524. (b) Mori, K. Tetrahedron 1973, 30, 1065-1072. (c) Galbraith, M. N.; Horn, D. H. S. J. Chem. Soc., Chem. Commun. 1973, 566-567. (d) Shibisaki, M.; Terashima, S.; Yamada, S. Chem. Pharm. Bull. 1976, 24, 315-322. (e) Kienzle, F.; Mayer, H.; Minder, R. E.; Thommen, H. Helv. Chim. Acta 1978, 61, 2616-2627. (f) Acemonglu, M.; Uebelhart, P.; Rey, M.; Eugster, C. H. Helv. Chim. Acta 1988, 71, 931-955. (g) Soukup, M.; Lukac, T.; Lohri, B.; Widmer, E. Helv. Chim. Acta 1989, 72, 361-364. (h) Sakai, K.; Takahashi, K.; Nukano, T. Tetrahedron 1992, 48, 8229-8238.
14. For (S)-(+)-ABA: (a) Oritani, T.; Yamashita, K. Tetrahedron Lett. 1972, 2521-2524. (b) Mori, K. Tetrahedron 1973, 30, 1065-1072. (c) Galbraith, M. N.; Horn, D. H. S. J. Chem. Soc., Chem. Commun. 1973, 566-567. (d) Shibisaki, M.; Terashima, S.; Yamada, S. Chem. Pharm. Bull. 1976, 24, 315-322. (e) Kienzle, F.; Mayer, H.; Minder, R. E.; Thommen, H. Helv. Chim. Acta 1978, 61, 2616-2627. (f) Acemonglu, M.; Uebelhart, P.; Rey, M.; Eugster, C. H. Helv. Chim. Acta 1988, 71, 931-955. (g) Soukup, M.; Lukac, T.; Lohri, B.; Widmer, E. Helv. Chim. Acta 1989, 72, 361-364. (h) Sakai, K.; Takahashi, K.; Nukano, T. Tetrahedron 1992, 48, 8229-8238.
15. For (S)-(+)-ABA: (a) Oritani, T.; Yamashita, K. Tetrahedron Lett. 1972, 2521-2524. (b) Mori, K. Tetrahedron 1973, 30, 1065-1072. (c) Galbraith, M. N.; Horn, D. H. S. J. Chem. Soc., Chem. Commun. 1973, 566-567. (d) Shibisaki, M.; Terashima, S.; Yamada, S. Chem. Pharm. Bull. 1976, 24, 315-322. (e) Kienzle, F.; Mayer, H.; Minder, R. E.; Thommen, H. Helv. Chim. Acta 1978, 61, 2616-2627. (f) Acemonglu, M.; Uebelhart, P.; Rey, M.; Eugster, C. H. Helv. Chim. Acta 1988, 71, 931-955. (g) Soukup, M.; Lukac, T.; Lohri, B.; Widmer, E. Helv. Chim. Acta 1989, 72, 361-364. (h) Sakai, K.; Takahashi, K.; Nukano, T. Tetrahedron 1992, 48, 8229-8238.
16. For (S)-(+)-ABA: (a) Oritani, T.; Yamashita, K. Tetrahedron Lett. 1972, 2521-2524. (b) Mori, K. Tetrahedron 1973, 30, 1065-1072. (c) Galbraith, M. N.; Horn, D. H. S. J. Chem. Soc., Chem. Commun. 1973, 566-567. (d) Shibisaki, M.; Terashima, S.; Yamada, S. Chem. Pharm. Bull. 1976, 24, 315-322. (e) Kienzle, F.; Mayer, H.; Minder, R. E.; Thommen, H. Helv. Chim. Acta 1978, 61, 2616-2627. (f) Acemonglu, M.; Uebelhart, P.; Rey, M.; Eugster, C. H. Helv. Chim. Acta 1988, 71, 931-955. (g) Soukup, M.; Lukac, T.; Lohri, B.; Widmer, E. Helv. Chim. Acta 1989, 72, 361-364. (h) Sakai, K.; Takahashi, K.; Nukano, T. Tetrahedron 1992, 48, 8229-8238.
17. For example: Aldrich Chemical Company, Milwaukee, WI; 1994-95 Catalog; (±)-ABA, $131/g; (S)-(+)-ABA, $167/mg.
18. Bonafous, J.-C.; Mani, J.-C.; Olivé, J.-L.; Mousseron-Canet, M. Tetrahedron Lett. 1973, 1119-1122 and cited references.
19. For an example: Dunstan, D. I.; Bock, C. A.; Abrams, G. D.; Abrams, S. R. Phytochemistry 1992, 31, 1451-1454.
20. See inter alia: (a) Todoroki, Y.; Nakano, S.-I.; Hirai, N.; Ohigashi, H. Tetrahedron 1996, 52, 8081-8098. (b) Lamb, N.; Wahab, N.; Rose, P. A.; Shaw, A. C.; Abrams, S. R.; Cutler, A. J.; Smith, P. J.; Gusta, L. V.; Ewan, B. Phytochemistry 1996, 41, 23-28.
21. See inter alia: (a) Todoroki, Y.; Nakano, S.-I.; Hirai, N.; Ohigashi, H. Tetrahedron 1996, 52, 8081-8098. (b) Lamb, N.; Wahab, N.; Rose, P. A.; Shaw, A. C.; Abrams, S. R.; Cutler, A. J.; Smith, P. J.; Gusta, L. V.; Ewan, B. Phytochemistry 1996, 41, 23-28.
22. For some exceptions, see: Lamb, N.; Abrams, S. R. Can. J. Chem. 1990, 68, 1151-1162 and cited references.
23. Assante, G.; Merlini, L; Nassini, G. Experientia 1977, 33, 1556.
24. Toray Industries Inc., Japan. We thank Toray and Dr. L. Gusta (Crop Development Center, University of Saskatchewan) for a generous gift of (S)-(+)-ABA.
25. Gusta, L. V.; Ewan, B.; Reaney, M. J. T.; Abrams, S. R. Can. J. Bot. 1992, 70, 1550-1555.
26. 2 was activated according to: Goldman, I. M. J. Org. Chem. 1969, 34, 1979-1981.
27. Ward, D. E.; Rhee, C. K. Synth. Commun. 1988, 18, 1927-1933; Can. J. Chem. 1989, 67, 1206-1211.
28. Ward, D. E.; Rhee, C. K. Synth. Commun. 1988, 18, 1927-1933; Can. J. Chem. 1989, 67, 1206-1211.
29. Larock, R. H. Comprehensive Organic Transformations; VCH: New York, 1989. pp 548-549 and 619-621.
30. Yoon, N. M.; Pak, C. S.; Brown, H. C.; Krishnamurthy, S.; Stocky, T. P. J. Org. Chem. 1973, 38, 2786-2797.
31. Lane, C. F.; Myatt, H. L.; Daniels, J.; Hopps, H. B. J. Org. Chem. 1974, 39, 3052-3054.
32. Ward, D. E.; Rhee, C. K.; Zoghaib, W. M. Tetrahedron Lett. 1988, 29, 517-520.
33. Raber, D. L.; Guida, W. C. J. Org. Chem. 1976, 41, 690-696.
34. Babler, J. H. Synth. Commun. 1982, 12, 839-846.
35. 3e
36. General procedures were recently described: Ward, D. E.; Nixey, T. E.; Gai, Y.; Hrapchak, M. J.; Abaee, M. S. Can. J. Chem. 1996, 74, 1418-1436.
37. Taber, D. F. J. Org. Chem. 1982, 47, 1351.
38. Still, W. C.; Kahn, M.; Mitra, A. J. Org. Chem. 1978, 43, 2923.
39. 3e for the racemic compound.