Total synthesis of the virginiamycin antibiotic 14,15-anhydropristinamycin IIB

Journal of the Chemical Society - Perkin Transactions 1

Volumn , Issue 12, 1996, Pages 1315-1317

  Entwistle, David A ^a   Jordan, Stuart I ^a   Montgomery, John ^a   Pattenden, Gerald ^a  

^a UNIVERSITY OF NOTTINGHAM   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33748893957     PISSN: 0300922X     EISSN: None     Source Type: Journal    
DOI: 10.1039/p19960001315     Document Type: Article

References (43)

1. C. Cocito, Microbiol. Rev., 1979, 43, 145;
2. J. M. Paris, J. C. Barrière, C. Smith and P. E. Bost, in Recent Progress in the Chemical Synthesis of Antibiotics, eds. G. Lucass and M. Ohno, Springer Verlag, Berlin, 1990, 183.
3. G. R. Delpierre, F. W. Eastwood, G. E. Gream, D. G. I. Kingston, P. J. Sarin, A. R. Lord Todd and D. H. Williams, J. Chem. Soc. C, 1966, 1653.
4. K. T. Lam, R. L. S. Chang, O. D. Hensens, C. D. Schwartz and D. L. Zink, USP 4 894 370;
5. see M. G. Bock, Drugs of the Future, 1991, 16, 631;
6. Y. K. Lam, D. Bogen, R. S. Chang, K. A. Faust, O. D. Hensens, D. L. Zink, C. D. Schwarz, L. Zitano, G. M. Garrity, M. M. Gagliardi, S. A. Currie and H. B. Woodruff, J. Antibiotics, 1991, 44, 613.
7. (a) R. D. Wood and B. Ganem, Tetrahedron Lett., 1983, 24, 4391;
8. (b) A. I. Meyers, J. P. Lawson, D. G. Walker and R. J. Linderman, J. Org. Chem., 1986, 51, 5111;
9. (c) L. Liu, R. S. Tanke and M. J. Miller, J. Org. Chem., 1986, 51, 5332;
10. (d) R. H. Schlessinger, E. J. Iwanowicz and J. P. Springer, Tetrahedron Lett., 1988, 29, 1489;
11. (e) N. Adje, P. Breuilles and D. Uguen, Tetrahedron Lett., 1993, 34, 4631;
12. (f) P. Helquist, M. Bergdahl, R. Hett, A. R. Gangloff, M. Demillequand, M. Cottard, M. M. Mader, T. Friebe, J. Iqbal, Y. Wu, B. Akermark, T. Rein and N. Kann, Pure Appl. Chem., 1994, 66, 2063; and earlier references cited therein.
13. After the completion of our work we were informed that A. I. Meyers et al. had completed a synthesis of (-)-madumycin II, and that R. H. Schlessinger et al. had completed a synthesis of virginiamycin M2 1. (We thank Professor Meyers for providing this information.) Following the acceptance of this paper these independent syntheses were published: R. H. Schlessinger and Y.-J. Li, J. Am. Chem. Soc., 1966, 118, 3301;
14. F. Tavares, J. P. Lawson and A. I. Meyers, J. Am. Chem. Soc., 1996, 118, 3303.
15. See: J. P. Michael and G. Pattenden, Angew. Chem., Int. Ed. Engl., 1993, 32, 1;
16. S. K. Chattopadhyay and G. Pattenden, Tetrahedron Lett., 1995, 36, 5271;
17. C. J. Boden and G. Pattenden, Tetrahedron Lett., 1995, 36, 6153 and references cited therein.
18. G. Pattenden and S. M. Thom, Synlett, 1993, 215;
19. R. J. Boyce and G. Pattenden, Tetrahedron Lett., 1996, 37, 3501;
20. see also C. Boden and G. Pattenden, Synlett, 1994, 181.
21. Some of the first examples of the intramolecular Stille reaction in synthesis were described by Piers et al., see: E. Piers, R. W. Friesen and B. A. Keay, J. Chem. Soc., Chem. Commun., 1985, 809;
22. E. Piers and R. W. Friesen, J. Org. Chem., 1986, 51, 3405;
23. E. Piers and Y.-F. Lu, J. Org. Chem., 1988, 53, 926;
24. see also: K. C. Nicolaou, T. K. Chakraborty, A. D. Piscopio, N. Minowa and P. Bertinato, J. Am. Chem. Soc., 1993, 115, 4419;
25. A. G. M. Barrett, M. L. Boys and T. L. Boehm, J. Org. Chem., 1996, 61, 685;
26. T. S. McDermott, A. A. Mortlock and C. H. Heathcock, J. Org. Chem., 1996, 61, 700;
27. R. M. Adlington, J. E. Baldwin, A. Gansäuer, W. McCoull and A. T. Russell, J. Chem. Soc., Perkin Trans. 1, 1994, 1697;
28. D. M. Hodgson, L. T. Boulton and G. N. Maw, Synlett, 1995, 267;
29. A. B. Smith, III, S. M. Condon, J. A. McCauley, J. L. Leazer, Jr., J. W. Leahy and R. E. Maleczka, J. Am. Chem. Soc., 1995, 117, 5407.
30. For reviews see: J. K. Stille, Angew. Chem., Int. Ed. Engl., 1986, 25, 508;
31. T. N. Mitchell, Synthesis, 1992, 803;
32. see also: J. K. Stille and M. Tanaka, J. Am. Chem. Soc., 1987, 109, 3785;
33. J. K. Stille, H. Su, D. H. Hill, P. Schneider, M. Tanaka, D. L. Morrison and L. S. Hegedus, Organometallics, 1991, 10, 1993;
34. A. C. Gyorkos, J. K. Stille and L. S. Hegedus, J. Am. Chem. Soc., 1990, 112, 8465;
35. A. Kalivretenos, J. K. Stille and L. S. Hegedus, J. Org. Chem., 1991, 56, 2883.
36. 1H NMR analysis of its Mosher ester. A. I. Meyers, R. F. Spohn and R. J. Linderman, J. Org. Chem., 1985, 50, 3633.
37. A. Basha, M. Lipton and S. M. Weinreb, Tetrahedron Lett., 1977, 48, 4171.
38. L. Capella, A. Degl Innocenti, A. Nordini, G. Reginato, A. Ricci and G. Seconi, Synthesis, 1991, 1201.
39. T. J. Curphey, J. Org. Chem., 1979, 44, 2805.
40. D -65.2 for natural L-proline trifluoroamide. A. Ookawa and K. Soai, J. Chem. Soc., Perkin Trans. 1, 1987, 1465.
41. E. J. Corey, M. G. Bock, A. P. Kozikowski, and A. V. Rama Rao, Tetrahedron Lett., 1978, 12, 1051.
42. Compound 11 was produced from the corresponding carboxylic acid ethyl ester (J. W. Cornforth and R. H. Cornforth, J. Chem. Soc., 1947, 96); by reduction with DIBAL ¶ at -78°C (75%).
43. 2 was somewhat fortuitous. The use of many other conventional oxidants instead led to complex mixtures of products in poor yields.