Catalytic enantioselective synthesis of macrolides via asymmetric alkylation

Tetrahedron Asymmetry

Volumn 8, Issue 11, 1997, Pages 1797-1809

  Jones, Graham B ^a   Huber, Robert S ^a   Chapman, Brant J ^a  

^a CLEMSON UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

LASIODIPLODIN; MACROLIDE; PHORACANTHOLIDE; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; DRUG SYNTHESIS; ENANTIOMER; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; STEREOCHEMISTRY;

EID: 0030956836     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(97)00186-9     Document Type: Article

References (27)

1. Representative examples: Masamune, S.; Lu, L. D.; Jackson, W. P.; Kaiho, T.; Toyoda, T. J. Am. Chem. Soc. 1982, 104, 5523; Stork, G.; Rychnovsky, S. J. Am. Chem. Soc. 1987, 109, 1565.
2. Representative examples: Masamune, S.; Lu, L. D.; Jackson, W. P.; Kaiho, T.; Toyoda, T. J. Am. Chem. Soc. 1982, 104, 5523; Stork, G.; Rychnovsky, S. J. Am. Chem. Soc. 1987, 109, 1565.
3. Corey, E. J.; Cheng, X.-M. The Logic of Chemical Synthesis; Wiley, New York, 1989.
4. For review see: Roxburgh, C. J.; Tetrahedron 1995, 51, 9767.
5. Jones, G. B.; Heaton, S. B. Tetrahedron Lett. 1992, 33, 1693.
6. Jones, G. B.; Heaton, S. B. Tetrahedron: Asymmetry 1993, 4, 261.
7. For representative syntheses see: (a) Gerlach, H.; Kunzler, P.; Oertle, K. Helv. Chim. Acta. 1978, 67, 1226;
8. (b) Nagumo, S.; Suemune, H.; Sakai, K. Tetrahedron. 1992, 48, 8667;
9. (c) Fouque, E.; Rousseau, G. Synthesis 1989, 661.
10. Dess, D. B.; Martin, J. C. J. Org. Chem. 1983, 48, 4156. For improved preparation of this reagent see: Ireland, R. E.; Liu, L.; J. Org. Chem. 1993, 58, 2899.
11. Dess, D. B.; Martin, J. C. J. Org. Chem. 1983, 48, 4156. For improved preparation of this reagent see: Ireland, R. E.; Liu, L.; J. Org. Chem. 1993, 58, 2899.
12. (a) Bessodes, M.; Komiotis, D.; Antonakis, K. Tetrahedron Lett. 1986, 27, 579;
13. (b) Koster, H.; Sinha, N. D. Tetrahedron Lett. 1982, 23, 2641.
14. Jones, G. B.; Chapman, B. J.; Huber, R. S.; Beaty, R. Tetrahedron: Asymmetry 1994, 5, 1199.
15. Corey, E. J.; Nicolaou, K. C. J. Am. Chem. Soc. 1974, 96, 5614.
16. Kitahara, T.; Koseki, K.; Mori, K. Agric. Biol. Chem. 1983, 47, 389.
17. Drager, G.; Kirschning, A.; Thiericke, R.; Zerlin, M. Nat. Prod. Reps. 1996, 13, 365.
18. Gerlach, H.; Thalman, A. Helv. Chim. Acta. 1977, 60, 2866; Takahashi, T.; Kasuga, K.; Tsuji, J. Tetrahedron Lett. 1978, 4917; Danishefsky, S. J.; Etheredge, S. J. J. Org. Chem. 1979, 44, 4716.
19. Gerlach, H.; Thalman, A. Helv. Chim. Acta. 1977, 60, 2866; Takahashi, T.; Kasuga, K.; Tsuji, J. Tetrahedron Lett. 1978, 4917; Danishefsky, S. J.; Etheredge, S. J. J. Org. Chem. 1979, 44, 4716.
20. Gerlach, H.; Thalman, A. Helv. Chim. Acta. 1977, 60, 2866; Takahashi, T.; Kasuga, K.; Tsuji, J. Tetrahedron Lett. 1978, 4917; Danishefsky, S. J.; Etheredge, S. J. J. Org. Chem. 1979, 44, 4716.
21. Aldridge, D. C.; Galt, S.; Giles, D.; Turner, W. B. J. Chem. Soc. (C) 1971, 1623.
22. (a) Braun, M.; Mahler, U.; Houben, S. Liebigs Ann. Chem. 1990, 513;
23. (b) Solladie, G.; Rubio, A.; Carreno, M. C.; Ruano, J. L. Tetrahedron: Asymmetry 1990, 1, 187.
24. Shekhani, M. S.; Khan, K. M.; Mahmood, K.; Shah, P. M.; Malik, S. Tetrahedron Lett. 1990, 31, 1669.
25. Kato, T.; Hozumi, T. Chem. Pharm. Bull. 1972, 20, 1574.
26. Jones, G. B.; Huber, R. S. Synlett. 1993, 367.
27. Jones, G. B.; Mathews, J. E. Bioorg. Med. Chem. Lett. 1995, 5, 93.