Application of arene-ruthenium chemistry to a formal total synthesis of OF 4949 III

Journal of Organic Chemistry

Volumn 61, Issue 19, 1996, Pages 6581-6586

  Pearson, Anthony J ^a   Zhang, Penglie ^a   Lee, Kieseung ^a  

^a CASE WESTERN RESERVE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

IMMUNOMODULATING AGENT; OF 4949 II; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0029836751     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo960956l     Document Type: Article

References (32)

1. (a) Sano, S.; Ikai, K.; Kuroda, H.; Nakamura, T.; Obayashi, A.; Ezure, Y.; Enomoto, H. J. Antibiot. 1986, 39, 1674.
2. (b) Sano, S.; Ikai, K.; Katayama, K.; Takesako, K.; Nakamura, T.; Obayashi, A.; Ezure, Y.; Enomoto, H. J. Antibiot. 1986, 39, 1685.
3. (c) Sano, S.; Ueno, M.; Katayama, K.; Nakamura, T.; Obayashi, A. J. Antibiot. 1986, 39, 1697.
4. (d) Sano, S.; Ikai, K.; Yoshikawa, Y.; Nakamura, T.; Obayashi, A. J. Antibiot. 1987, 40, 512.
5. Nishiyama, S.; Suzuki, Y.; Yamamura, S. Tetrahedron Lett. 1988, 29 , 559.
6. Schmidt, U.; Weller, D.; Holder, A.; Lieberknecht, A. Tetrahedron Lett. 1988, 29 , 3227.
7. Evans, D. A.; Ellman, J. A. J. Am. Chem. Soc. 1989, 111, 1063.
8. Boger, D. L.; Yohannes, D. J. Org. Chem. 1990, 55, 6000.
9. For recent examples of Zhu's work, see: (a) Zhu, J.; Bouillon, J.-P.; Singh, G. P.; Chastanet, J.; Beugelmans, R. Tetrahedron Lett. 1995, 36, 7081.
10. (b) Neuville, L.; Bois-Choussy, M.; Zhu, J. Tetrahedron Lett. 1995, 36, 8787.
11. Mann, M. J.; Pant, N.; Hamilton, A. D. J. Chem. Soc., Chem. Commun. 1986, 158.
12. Hobbs, D. W.; Still, W. C. Tetrahedron Lett. 1987, 28, 2805.
13. Crimmin, M. J.; Brown, A. G. Tetrahedron Lett. 1990, 31, 2017.
14. Jung, M. E.; Starkey, L. S. Tetrahedron Lett. 1995, 36, 7363.
15. (a) Rao, A. V. R.; Gurjar, M. K.; Reddy, A. B.; Khare, V. B. Tetrahedron Lett. 1993, 34, 1657.
16. (b)Rao, A. V. R.; Gurjar, M. K.; Kaiwar, V.; Khare, V. B. Tetrahedron Lett. 1993, 34, 1661.
17. (a) Feng, X.; Olsen, R. K. J. Org. Chem. 1992, 57, 5811.
18. (b) Olsen, R. K.; Feng, X.; Campbell, M.; Shao, R.-L.; Math, S. K. J. Org. Chem. 1995, 50, 6025.
19. (a) Pearson, A. J.; Bruhn, P. R. J. Org. Chem. 1991, 56, 7092.
20. (b) Pearson, A. J.; Shin, H. J. Org. Chem. 1994, 59, 2314.
21. (c) Pearson, A. J.; Shin, H. Tetrahedron Lett. 1992, 48, 7527.
22. (d) Pearson, A. J.; Park, J. G.; Zhu, P. Y. J. Org. Chem. 1992, 57, 3583.
23. (e) Pearson, A. J.; Lee, K. J. Org. Chem. 1994, 59, 2304.
24. (f) Pearson, A. J.; Lee, K. J. Org. Chem. 1995, 60, 7153 .
25. (g) Pearson, A. J.; Bignan, G. Tetrahedron Lett. 1996,37, 735.
26. (h) Pearson, A. J.; Bignan, G.; Zhang, P.; Chelliah, M. J. Org. Chem. 1996, 61, 3941.
27. Ono, N.; Yamada, T.; Saito, T. Bull. Chem. Soc. Jpn. 1978, 51, 2401
28. A new Pd-catalyzed desilylation of phenolic TBDMS ethers has been reported recently. Wilson, N. S.; Keay, B. A. Tetrahedron Lett. 1996, 37, 153.
29. Pearson, A. J.; Lee, K J. Org. Chem. 1994, 59, 225.
30. (a) Williams, D. H.; Kalman J. R. J. Am. Chem. Soc. 1980, 102, 897.
31. (b) Williams, D. H.; Williamson, M. P. J. Chem. Soc., Perkin Trans. 1 1985, 949.
32. Kofron, W. G.; Baclawski, L. M. J. Org. Chem. 1976, 41, 1879.