Synthesis of 4-alkyl-4-alkoxybutenolides having unsaturated side chains via chromium carbene complex photochemistry: (+)-cerulenin

Journal of Organic Chemistry

Volumn 61, Issue 18, 1996, Pages 6121-6126

  Kedar, Tracey E ^a   Miller, Michael W ^a   Hegedus, Louis S ^a  

^a Department of Environmental and Radiological Health Sciences   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIFUNGAL AGENT; BUTENOLIDE; CERULENIN;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; PHOTOCHEMISTRY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0029790961     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo960664k     Document Type: Article

References (29)

1. DeGuzman, F. S.; Schmitz, F. J. J. Nat. Prod. 1990, 53, 926.
2. Ohta, T.; Tsuchiyama, H.; Nozoe, S. Heterocycles 1986, 24, 1137.
3. Maeba, I.; Suzuki, M.; Hara, O.; Takeuchi, T.; Iijima, T.; Furukawa, H. J. Org. Chem. 1987, 52, 4521.
4. Lopez Aparicio, F. J.; Lopez Sastre, J. A.; Garcia, J. I.; Diaz, R. R. Carbohydr. Res. 1984, 132, 19.
5. (a) Hegedus, L. S.; Bates, R. W.; Soderberg, B. C. J. Am. Chem. Soc. 1991, 113, 923.
6. (b) Reed, A. D.; Hegedus, L. S. J. Org. Chem. 1995, 60, 3787.
7. Miller, M. W.; Hegedus, L. S. J. Org. Chem. 1993, 58, 6779.
8. Valenti, E.; Pericas, M. A.; Moyano, A. J. Org. Chem. 1990, 55, 3582.
9. Franck-Neumann, M.; Martina, D.; Heitz, M. P. Tetrahedron Lett. 1982, 23, 3493.
10. Corey, E. J.; Williams, D. R. Tetrahedron Lett. 1977, 3847.
11. Moser, W. A.; Hegedus, L. S. J. Am. Chem. Soc. Submitted for publication.
12. Soderberg, B. C.; Hegedus, L. S.; Sierra, M. A. J. Am. Chem. Soc. 1990, 112, 4364.
13. Rajaram, J.; Narula, A. P. S.; Chawla, H. P. S.; Dev, Sukh. Tetrahedron 1983, 39, 2315.
14. For reviews, see: (a) Semmelhack, M. F. Org. React. 1972, 19, 115. (b) Billington, D. C. Chem. Soc. Rev. 1985, 14, 93.
15. For reviews, see: (a) Semmelhack, M. F. Org. React. 1972, 19, 115. (b) Billington, D. C. Chem. Soc. Rev. 1985, 14, 93.
16. Arison, B. H.; Omura, S. J. Antibiot. Ser. A 1974, 27, 28.
17. Sueda, N.; Ohrui, H.; Kuzuhara, H. Tetrahedron Lett. 1979, 2039.
18. Pietraszkiewicz, M.; Sinäy, P. Tetrahedron Lett. 1979, 4741.
19. Morisaki, N.; Funabashi, H.; Furukawa, J.; Shimazawa, R.; Kanematsu, A.; Ando, T.; Okuda, S.; Iwasaki, S. Chem. Pharm. Bull. 1992, 40, 2945.
20. Yoda, H.; Katagiri, T.; Takabe, K. Tetrahedron Lett. 1991, 32, 6771.
21. Graf, R. E.; Lillya, C. P. J. Organomet. Chem. 1976, 122, 377.
22. Matsumoto, M.; Kobayashi, H. Heterocycles 1986, 24, 2443.
23. Itsuno, S.; Hirao, A.; Nakahama, S.; Yamazaki, N. J. Chem. Soc., Perkin Trans, 1 1983, 1673.
24. Hoye, T. R; Chen, K.; Vyvyan, J. R. Organametallics 1993, 12, 2806.
25. Montgomery, J.; Wieber, G. M.; Hegedus, L. S. J. Am. Chem. Soc. 1990, 112, 6255.
26. Krysan, D. J.; Mackenzie, P. B. J. Org. Chem. 1990, 55, 4229.
27. Semmelhack, M. F. Org. React. 1972, 19, 115.
28. (a) Jakubowski, A. A.; Guziec, F. S.; Sugiura, M.; Tam, C. C.; Tischler, M.; Omura, S. J. Org. Chem. 1982, 47, 1221.
29. (b) Funabashi, H.; Iwasaki, S.; Okuda, S. Tetrahedron Lett. 1983, 24, 2673.