Asymmetric hydrogen transfer protocol for a synthesis of (+)-frontalin and (-)-malyngolide

Tetrahedron Letters

Volumn 41, Issue 19, 2000, Pages 3631-3635

  Mikie Kanada, Regina ^a   Taniguchi, Takahiko ^a   Ogasawara, Kunio ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

Asymmetric reaction; Epoxides; Natural products; Radicals and radical compounds; Ruthenium and compounds

Indexed keywords

EPOXIDE; FRONTALIN; MALYNGOLIDE; NATURAL PRODUCT; PHEROMONE; RUTHENIUM DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL REACTION; ENANTIOMER; NONHUMAN; OXIDATION; PROTON TRANSPORT; STEREOCHEMISTRY; SYNTHESIS;

EID: 0342699502     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00430-5     Document Type: Article

References (32)

1. Kanada, R. M.; Taniguchi, T.; Ogasawara, K. Chem. Commun. 1998, 1755.
2. Iura, Y.; Sugahara, T.; Ogasawara, K. Tetrahedron Lett. 1999, 40, 5735.
3. Hashiguchi, S.; Fujii, A.; Haack, K.-J.; Matsumura, K.; Ikariya, T.; Noyori, R. Angew. Chem., Int. Ed. Engl. 1997, 36, 288.
4. Haack, K.-J.; Hashiguchi, S.; Fujii, A.; Ikariya, T.; Noyori, R. Angew. Chem., Int. Ed. Engl. 1997, 36, 285.
5. Tanaka, K.; Ogasawara, K. Synthesis 1995, 1237.
6. Kanada, R. M.; Taniguchi, T.; Ogasawara, K., unpublished observation.
7. Takano, S.; Inomata, K.; Ogasawara, K. J. Chem. Soc., Chem. Commun. 1989, 271.
8. (a) Taniguchi, T.; Nakamura, K.; Ogasawara, K. Synthesis 1997, 509 and references cited therein. More recent synthesis:
9. (b) Maezaki, N.; Shogaki, T.; Uchida, M.; Tokuno, K.; Imamura, T.; Tanaka, T.; Iwata, C. Chem. Pharm. Bull. 1998, 46, 217.
10. (c) Nishimura, Y.; Mori, K. Eur. J. Org. Chem. 1998, 233.
11. (d) Mori, K. Eur. J. Org. Chem. 1998, 1479.
12. (e) Kouklovsky, C.; Dirat, O.; Berranger, T.; Langlois, Y.; Tranhuudau, M. E.; Riche, C. J. Org. Chem. 1998, 63, 5123.
13. (f) Majewski, M.; Nowak, P. Tetrahedron: Asymmetry 1998, 9, 2611.
14. (g) Mori, K. Chirality 1998, 10, 578.
15. (h) Scholl, M.; Grubbs, R. H. Tetrahedron Lett. 1999, 40, 1425.
16. (i) List, B.; Shabat, D.; Zhong, G. F.; Turner, J. M.; Li, A.; Bui, T.; Anderson, J.; Lerner, R. A.; Barbas, C. F. J. Am. Chem. Soc. 1999, 121, 7283.
17. (a) Konno, H.; Hiroya, K.; Ogasawara, K. Tetrahedron Lett. 1997, 38, 6023 and references cited therein. More recent synthesis:
18. (b) Maezaki, N.; Matsumori, Y.; Shogaki, T.; Soejima, M.; Tanaka, T.; Ohnishi, H.; Iwata, C. Chem. Commun. 1997, 1755.
19. (c) Ohira, S.; Ida, T.; Moritani, M.; Hasegawa, T. J. Chem. Soc., Perkin Trans. 1 1998, 293.
20. (d) Matsuo, K.; Matsumoto, T.; Nishiwaki, K. Heterocycles 1998, 48, 1213.
21. (e) Winter, E.; Hoppe, D. Tetrahedron 1998, 54, 10329.
22. (f) Maezaki, N.; Matsumori, Y.; Shogaki, T.; Soejima, M.; Ohnishi, H.; Tanaka, T.; Iwata, C. Tetrahedron 1998, 54, 13087.
23. Miller, R. D.; Dolce, D. L.; Merritt, V. Y. J. Org. Chem. 1976, 41, 1221.
24. Shimada, J.; Hashimoto, K.; Kim, B.H.; Nakamura, E.;Kuwajima, I.; J. Am. Chem. Soc. 1984, 106, 1759. Crane, S. N.; Jenkins, T. J.; Burnell, D. J. J. Org. Chem. 1997, 62, 8722.
25. Shimada, J.; Hashimoto, K.; Kim, B.H.; Nakamura, E.;Kuwajima, I.; J. Am. Chem. Soc. 1984, 106, 1759. Crane, S. N.; Jenkins, T. J.; Burnell, D. J. J. Org. Chem. 1997, 62, 8722.
26. Takano, S.; Inomata, K.; Ogasawara, K. J. Chem. Soc., Chem. Commun. 1992, 169.
27. Ogasawara, K. J. Syn. Org. Chem. Jpn. 1996, 54, 29.
28. Nahm, S.; Weinreb, S. M. Tetrahedron Lett. 1981, 22, 3815.
29. Matsuo, K.; Tanaka, K. Chem. Pharm. Bull. 1981, 29, 3070. Asaoka, M.; Hayashibe, S.; Sonoda, S.; Takei, H. Tetrahedron 1991, 47, 6967.
30. Matsuo, K.; Tanaka, K. Chem. Pharm. Bull. 1981, 29, 3070. Asaoka, M.; Hayashibe, S.; Sonoda, S.; Takei, H. Tetrahedron 1991, 47, 6967.
31. Takano, S.; Inomata, K.; Ogasawara, K. J. Chem. Soc., Chem. Commun. 1989, 271.
32. Barton, D. H. R.; Jang, D. O.; Jaszberenyi, J. C. Tetrahedron Lett. 1991, 32, 7187.