Enantioselective approaches to aminocyclopentitols: A total synthesis of (+)-6-epitrehazolin and a formal total synthesis of (+)-trehazolin

Journal of Organic Chemistry

Volumn 63, Issue 10, 1998, Pages 3403-3410

  Li, Jun ^a   Lang, Fengrui ^a   Ganem, Bruce ^a  

^a Department of Molecular Biology and Genetics   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

GLYCOSIDASE INHIBITOR; INSECTICIDE;

ARTICLE; ENZYME INHIBITION; INSECT CONTROL; STEREOCHEMISTRY; SYNTHESIS;

EID: 0032524799     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo980050a     Document Type: Article

References (42)

1. (a) McGarvey, G. J.; Wong, C.-H. Liebigs. Ann. / Receuil 1997, 1059-1074.
2. (b) Winchester, B.; Fleet, G. W. J. Glycobiology 1992, 2, 199-210.
3. (a) Aoyagi, T.; Yamamoto, T.; Kojiri, K.; Morishima, H.; Nagai, M.; Hamada, M.; Takeuchi, T.; Umezawa, H. J. Antibiot. 1989, 42, 883-889.
4. (b) Morishima, H.; Kojiri, K.; Yamamoto, T.; Aoyagi, T.; Nakamura, H.; Iitaka, Y. J. Antibiot. 1989, 42, 1008-1011.
5. (a) Sakuda, S.; Isogai, A.; Matsumoto, S.; Suzuki, A.; Koseki, K.; Kodama, H.; Suzuki, A. Agric. Biol. Chem. 1987, 51, 3251-3259.
6. (b) Sakuda, S.; Isogai, A.; Makita, T.; Matsumoto, S.; Suzuki, A.; Koseki, K.; Kodama, H.; Yamada, Y. Agric. Biol. Chem. 1988, 52, 1615-1617.
7. Ando, O.; Satake, H.; Itoi, K.; Sato, A.; Nakajima, M.; Takahashi, S.; Haruyama, H.; Okuma, Y.; Kinoshita, Y.; Enokita, R. J. Antibiot. 1991, 44, 1165-1168.
8. Asano, N.; Takeuchi, M.; Kameda, Y.; Matsui, K.; Kono, Y. J. Antibiot. 1990, 43, 722-726.
9. Vértesy, L.; Fehlhaber, H.-W.; Schulz, A. Angew. Chem., Int. Ed. Engl. 1994, 33, 1844-46.
10. Murao, S.; Miyata, S. Agric. Biol. Chem. 1980, 44, 219-221.
11. Elbein, A. D. Adv. Carbohydr. Chem. Biochem. 1974, 30, 227-256.
12. (a) Knapp, S.; Purandare, A.; Rupitz, K.; Withers, S. G. J. Am. Chem. Soc. 1994, 116, 7461-7462.
13. (b) Shiozaki, M.; Arai, M.; Kobayashi, Y.; Kasuya, A.; Miyamoto, S.; Furukawa, Y.; Takayama, T.; Haruyama, H. J. Org. Chem. 1994, 59, 4450-4460.
14. (c) Miyazaki, H.; Kobayashi, Y.; Shiozaki, M.; Ando, M.; Nakajima, M.; Hanzawa, H.; Haruyama, H. J. Org. Chem. 1995, 60, 6103-6109.
15. (a) Shiozaki, M.; Kobayashi, Y.; Aral, M.; Haruyama, H. Tetrahedron Lett. 1994, 35, 887-890.
16. (b) Shiozaki, M.; Arai, M.; Kobayashi, Y.; Kasuya, A.; Miyamoto, S. J. Org. Chem. 1994, 59, 4450-4460.
17. (a) Uchida, C.; Kitahashi, H.; Watanabe, S.; Ogawa, S. J. Chem. Soc., Perkin Trans. 1 1995, 1707-1717.
18. (b) Uchida, C.; Yamagishi, T.; Kitahashi, H.; Iwaisaki, Y.; Ogawa, S. Bioorg. Med. Chem. Lett. 1995, 3, 1605-1524.
19. (c) Uchida, C.; Kimura, H.; Ogawa, S. Bioorg. Med. Chem. Lett. 1997, 5, 921-939.
20. (a) Kobayashi, Y.; Miyazaki, H.; Shiozaki, M. J. Am. Chem. Soc. 1992, 114, 10065-10066.
21. (b) Kobayashi, Y.; Miyazaki, H.; Shiozaki, M. J. Org. Chem. 1994, 59, 813-822.
22. (a) Ogawa, S.; Uchida, C. Chem. Lett. 1993, 173-176.
23. (b) Uchida, C.; Yamagishi, T.; Ogawa, S. J. Chem. Soc., Perkin Trans. 1 1994, 589-602.
24. Goering, B. K.; Li, J.; Ganem, B. Tetrahedron Lett. 1995, 36, 8905-8908.
25. Ledford, B. E.; Carreira, E. M. J. Am. Chem. Soc. 1995, 117, 11811-11812.
26. (a) Ito, H.; Motoki, Y.; Taguchi, T.; Hanzawa, Y. J. Am. Chem. Soc. 1993, 115, 8835-8836.
27. (b) Perrin, E.; Mallet, J.-M.; Sinay, P. Carbohydr. Lett. 1995, 1, 215-216.
28. (c) Marco-Contelles, J.; Destabel, C.; Gallego, P.; Chiara, J. L.; Bernabé, M. J. Org. Chem. 1996, 61, 1354-1362.
29. (a) Hasegawa, A.; Sable, H. Z. J. Org. Chem. 1966, 31, 4154-4161.
30. (b) Steyn, R.; Sable, H. Z. Tetrahedron 1969, 25, 3579-3597.
31. Goering, B. K.; Ganem, B. Tetrahedron Lett 1994, 35, 6997-7000.
32. King, S. B.; Ganem, B. J. Am. Chem. Soc. 1994, 116, 562-570.
33. Nichols, J.; Tralka, T.; Goering, B. K.; Wilcox, C. F.; Ganem, B. Tetrahedron 1996, 52, 3355-3364.
34. (a) Camarasa, M. J.; Fernandez-Resa, P.; Garcia-Lopez, M. T.; De las Heras, F. G.; Mendez-Castrillon, P. P.; Felix, A. S. Synthesis 1984, 509-510.
35. (b) review: Witczak, Z. J. Adv. Carbohydr. Chem. Biochem. 1986, 44, 91-145.
36. Corey, E. J.; Koelliker, U.; Neuffer, J. J. Am. Chem. Soc. 1971, 1489-1490.
37. Grieco, P. A.; Gilman, S.; Nishizawa, M. J. Org. Chem. 1976, 41, 1485-1486.
38. Berti, G. Topics Stereochem. 1973, 7, 93-251.
39. Rozen, S.; Bareket, Y.; Dayan, S. Tetrahedron Lett. 1996, 37, 531-534.
40. (a) Franks, J. A., Jr.; Tolbert, B.; Steyn, R.; Sable, H. Z. J. Org. Chem. 1965, 30, 1440-1446.
41. (b) Tolbert, B.; Steyn, R.; Franks, J. A., Jr.; Sable H. Z. Carbohydr. Res. 1967, 5, 62-81.
42. For general experimental procedures, see ref 19.