Novel, Enantioselective Lactone Construction. First Synthesis of Methylenolactocin, Antitumor Antibiotic from Penicillium sp.

Journal of Organic Chemistry

Volumn 57, Issue 17, 1992, Pages 4567-4569

  de Azevedo, Mariangela B M ^a   Murta, Maria M ^a   Greene, Andrew E ^a  

^a UNIV GRENOBLE ALPES   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIBIOTIC AGENT; METHYLENOLACTOCIN; UNCLASSIFIED DRUG;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS;

EID: 0026782629     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00043a003     Document Type: Letter

References (57)

1. Yoshioka, H.; Mabry, T. J.; Timmermann, B. N. Sesquiterpene Lactones; University of Tokyo Press: Tokyo, 1973.
2. Grieco, P. A. Synthesis 1975, 67-82.
3. Heywood, H.; Harbome, J. B.; Turner, B. L. The Biology and Chemistry of the Compositae; Academic Press: London, 1977; Vols. 1 and 2.
4. Fischer, N. H.; Oliver, E. J.; Fischer, H. D. In Progress in the Chemistry of Organic Natural Products; Here, W., Grisebach, H., Kirby, G. W., Eds.; Springer-Verlag: New York, 1979; Vol. 38, Chapter 2.
5. Hoffmann, H. M. R.; Rabe, J. Angew. Chem., Int. Ed. Engl. 1985, 24, 94-110.
6. Petragnani, N.; Ferraz, H. M. C.; Silva, G. V. J. Synthesis 1986,157-183.
7. Mukaiyama, T.; Suzuki, K. Chem. Lett. 1980, 255-256.
8. Takano, S.; Imamura, Y.; Ogasawara, K. Tetrahedron Lett. 1981, 22, 4479-4482.
9. Toda, F.; Tanaka, K.; Omata, T.; Nakamura, K.; Oshima, T. J. Am. Chem. Soc. 1983, 105, 5151-5152.
10. Marino, J. P.; Perez, A. D. J. Am. Chem. Soc. 1984, 106, 7643-7644.
11. Kosugi, H.; Konta, H.; Uda, H. J. Chem. Soc., Chem. Commun. 1985,211-213.
12. Thijs, L.; Waanders, P. P.; Stokkingreef, E. H. M.; Zwanenburg, B. Reel. Trav. Chim. Pays-Bas 1986, 105, 332-337.
13. Marino, J. P.; Laborde, E.; Paley, R. S. J. Am. Chem. Soc. 1988, 110, 966-968.
14. Salaun, J.; Karkour, B. Tetrahedron Lett. 1988, 29, 1537-1540.
15. Hoppe, D.; Zschage, O. Angew. Chem., Int. Ed. Engl. 1989, 28, 69-71.
16. Chong, J. M.; Mar, E. K. Tetrahedron Lett. 1990, 31, 1981-1984.
17. Ohkuma, T.; Kitamura, M.; Noyori, R. Tetrahedron Lett. 1990, 31, 5509-5512.
18. Kitamura, M.; Tokunaga, M.; Ohkuma, T.; Noyori, R. Tetrahedron Lett. 1991, 32, 4163-4166.
19. Doyle, M. P.; van Oeveren, A.; Westrum, L. J.; Protopopova, M. N.; Clayton, T. W., Jr. J. Am. Chem. Soc. 1991,113, 8982-8984.
20. Park, B. K.; Nakagawa, M.; Hirota, A.; Nakayama, M. J. Antibiot. 1988, 41, 751-758.
21. Nakayama, M.; Nakagawa, S.; Boku, T.; Hirota, A.; Shima, S.; Nakanishi, O.; Yamada, Y. Jpn. Kokai Tokhyo Koho 1989,1, 16,776.
22. Nakayama, M.; Nakagawa, S.; Boku, T.; Hirota, A.; Shima, S.; Nakanishi, O.; Yamada, Chem. Abstr. 1990,112, 34404f.
23. Greene, A. E.; Charbonnier, F. Tetrahedron Lett. 1985,26, 5525-5528.
24. Greene, A. E.; Charbonnier, F.; Luche, M.-J.; Moyano, A. J. Am. Chem. Soc. 1987,109,4752-4753.
25. Fráter, G.; Müller, U.; Günther, W. Helv. Chim. Acta 1986, 69, 1858-1861.
26. Whitesell, J. K.; Chen, H. H.; Lawrence, R. M. J. Org. Chem. 1985, 50, 4663-4664.
27. Whitesell, J. K.; Lawrence, R. M. Chimica 1986, 40, 318-321.
28. Schwartz, A.; Madan, P.; Whitesell, J. K.; Lawrence, R. M. Org. Synth. 1990, 69,1-9.
29. Okazoe, T.; Takai, K.; Oshima, K.; Utimoto, K. J. Org. Chem. 1987, 52, 4410-4412.
30. Villieras, J.; Bacquet, C.; Normant, J.-F. Bull. Soc. Chim. Fr. 1975,1797-1802.
31. Fischer, P. In Chemistry of Ethers, Crown Ethers, Hydroxyl Groups, and Their Sulphur Analogues; Patai, S., Ed.; John Wiley and Sons: New York, 1980; Vol. 2, Chapter 17.
32. Whitesell, J. K.; Lawrence, R. M.; Chen, H. J. Org. Chem. 1986, 51, 4779-4784.
33. Krepski, L. R.; Hassner, A. J. Org. Chem. 1978, 43, 3173-3179.
34. Belluš, D.; Ernst, B. Angew. Chem., Int. Ed. Engl. 1988,27, 797-827.
35. Kochi, J. K.; Singleton, D. M. J. Am. Chem. Soc. 1968, 90, 1582-1589.
36. Wade, R. S.; Castro, C. E. Org. Synth. 1972, 52, 62-66.
37. Carleen, P. H. J.; Katsuki, T.; Martin, V. S.; Sharpless, K. B. J. Org. Chem. 1981,46, 3936-3938.
38. Nunez, M. T.; Martin, V. S. J. Org. Chem. 1990, 55, 1928-1932.
39. van Tamelen, E. E.; Bach, S. R. J. Am. Chem. Soc. 1958,80, 3079-3086.
40. Martin, J.; Watts, P. C.; Johnson, F, J. Org. Chem. 1974, 39, 1676-1681.
41. Cavallito, C. J.; Fruehauf, McK. D.; Bailey, J. H. J. Am. Chem. Soc. 1948, 70, 3724-3726.
42. Carlson, R. M.; Oyler, A. R. J. Org. Chem. 1976, 41, 4065-4069.
43. Danishefsky, S.; Kitahara, T.; McKee, R.; Schuda, P. F. J. Am. Chem. Soc. 1976, 98, 6715-6717.
44. Roberts, J. L.; Borromeo, P. S.; Poulter, C. D. Tetrahedron Lett. 1977, 1621-1624.
45. Grieco, P.; Hiroi, K. J. Chem. Soc., Chem. Commun. 1972, 1317-1318.
46. Danishefsky, S.; Hirama, M.; Gombatz, K.; Harayama, T.; Berman, E.; Schuda, P. J. Am. Chem. Soc. 1979,101, 7020-7031.
47. Stiles, M. J. Am. Chem. Soc. 1959, 81, 2598-2599.
48. Finkbeiner, H. L.; Stiles, M. J. Am. Chem. Soc. 1963, 85, 616-622.
49. Gras, J.-L. Tetrahedron Lett. 1978, 2111-2114.
50. Okada, K.; Okubo, K.; Oda, M. Tetrahedron Lett. 1989, 40, 6733-6736.
51. Ravid, U.; Silverstein, R. M.; Smith, L. R. Tetrahedron 1978,34, 1449-1452.
52. Asahina, Y.; Asano, M. J. Pharm. Soc. Jpn. 1927, 539,1-17.
53. Asano, M.; Azumi, T. Chem. Ber. 1935, 68B, 995-997.
54. Asahina, Y.; Yanagita, M. Chem. Ber. 1936, 69B, 120-125.
55. Asahina, Y.; Yanagita, M.; Sakurai, Y. Chem. Ber. 1937, 70B, 227-235.
56. Brookes, D.; Tidd, B. K.; Turner, W. B. J. Chem. Soc. 1963, 5385-5391.
57. McCorkindale, N. J.; Wright, J. L. C.; Brian, P. W.; Clarke, S. M.; Hutchinson, S. A. Tetrahedron Lett. 1968, 727-730.