Laboratory emulation of polyketide biosynthesis: An iterative, aldol-based, synthetic entry to polyketide libraries using (R)- And (S)-l-(benzyloxy)-2-methylpentan-3-one, and conformational aspects of extended polypropionates

Journal of the Chemical Society - Perkin Transactions 1

Volumn , Issue 8, 1999, Pages 1003-1014

  Paterson, Lan ^a   Scott, Jeremy P ^a  

^a UNIVERSITY OF CAMBRIDGE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33746591212     PISSN: 0300922X     EISSN: None     Source Type: Journal    
DOI: 10.1039/a809818b     Document Type: Article

References (52)

1. (a) i. A. Ellmann and M. A. Gallop, Curr. Opin. Chein. Biol., 1998, 2, 317;
2. (b) L. A. Thompson and J. A. Ellmann, Chem. Rer., 1996, 96, 555.
3. D. O'Hagan, The Polyketiile Afetabolites, Ellis Horwood, Chichester, 1991.
4. (a) L. Katz, Client. Rer., 1997, 97, 2557;
5. (h) P. F. Leadlay, Curr. Opin. Chcm. Biol, 1997, 1, 162;
6. C. Khosla, Clicintracls-Org. Chcni., 1998, 11, 1.
7. (a) i. Staunton, Augen: Client., Int. Ed. Engl., 1991, 30, 1302;
8. (h) J. A. Robinson, in Progress in Natural Product Chemistry, vol. 58, pp. 1-81, eds. W. Herz, G. W. Kirby, W. Steglich and C. Tamm, Springer-Verlag, Wien, New York, 1991;
9. D. E. Cane, Science, 1994, 263, 338.
10. (a) M. J. B. Brown, J. Cortes, A. L. Cutter, P. F. Leadlay and J. Staunton, J. Chem. Soc., Chem. Commun., 1995, 1517;
11. (b) ). Cortes, K. E. H. Wiesmann, G. A. Roberts, M. J. B. Brown, J. Staunton and P. F. Leadlay, Science, 1995, 268, 1487;
12. R. Pieper, G. Luo, D. E. Cane and C. Khosla, J. Am. Chem. Soc., 1995, 117, 11373;
13. C. M. Kao, G. Luo, L. Katz, D. E. Cane and C. Khosla, J Am. Chem. Soc., 1996, 118, 9184.
14. (a) Aplyronines: I. Paterson, C. J. Cowden and M. D. Woodrow, Tetrahedron Lett., 1998, 39, 6037;
15. (b) Scytophycin C: I. Paterson, C. Watson, K.-S. Yeung, P. A. Wallace and R. A. Ward, J. Org. Chem., 1997, 62, 452;
16. Restricticin: I. Paterson and T. Nowak, Tetrahedron Lett., 1996, 37, 8243;
17. Swinholide A: I. Paterson, K.-S. Yeung, R. A. Ward, J. G. Cumming and J. D. Smith, J. Am. Chem. Soc., 1994, ', 116, 9391;
18. (e) Oleandolide: I. Paterson, R. D. Norcross, R. A. Ward, P. Romea and M. A. Lister, J. Am. Chem. Soc.; 1994, 116, 11287;
19. (/) Muamvatin: I. Paterson and M. V. Perkins, ./ Am. Chem. Soc., 1993, 115, 1608.
20. (a) I. Paterson, J. M. Goodman and M. Isaka, Tetrahedron Lett., 1989, 30, 7121;
21. (b) I. Paterson and M. A. Lister, Tetrahedron Lett., 1988, 29, 585;
22. I. Paterson and R. D. Tillyer, Tetrahedron Lett., 1992, 33, 4233;
23. I. Paterson and J. A. Channon, Tetrahedron Lett., 1992, 33, 797.
24. (a) I. Paterson and M. D. McLeod, Tetrahedron Lett., 1997, 38, 4183;
25. (b) I. Paterson and M. V. Perkins, Tetrahedron, 1996, 52, 1811;
26. I. Paterson and S. P. Wren, J. Chem. Soc., Chem. Commun., 1993, 1790.
27. Part of this work has appeared as preliminary communications:
28. (a) I. Paterson and J. P. Scott, Tetrahedron Lett., 1997, 38, 7441;
29. (b) I. Paterson and J. P. Scott, Tetrahedron Lett., 1997, 38, 7445.
30. A. J. Mancuso and D. Swern, Synthesis, 1981, 165.
31. (a) W. Roush, J. Org. Chem., 1991, 56, 4151;
32. (b) C. Gennari, A. Comotti, A. Vulpetti, J. M. Goodman and I. Paterson, Tetrahedron, 1992, 48, 4439.
33. (a) S. D. Rychnovsky and D. J. Skalitzky, Tetrahedron Lett., 1990, 31, 945;
34. (b) D. A. Evans, D. L. Rieger and J. R. Gage, Tetrahedron Lett., 1990, 31, 7099;
35. S. D. Rychnovsky, B. N. Rogers and T. I. Richardson, Ace. Chem. Res., 1998, 31, 9.
36. C. Gennari, S. Ceccarelli, U. Piarulli, K. Aboutayab, M. Donghi and I. Paterson, Tetrahedron, 1998, 54, 14999. For an approach using the Evans oxazolidinone auxiliary, see: (a) M. Reggelin and V. Brenig, Tetrahedron Lett., 1996, 38, 6851;
37. (b) M. Reggelin, V. Brenig and R. Welcker, Tetrahedron Lett., 1998, 39, 4801.
38. D. A. Evans, K. T. Chapman and E. M. Carreira, J. Am. Chem. Soc., 1988, 110, 3560.
39. I. Ohtani, T. Kusumi, Y. Kashman and H. Kakisawa, J. Am. Chem. Soc., 1991, 113, 4092.
40. Paterson and R. D. Tillyer, J. Org. Chem., 1993, 58, 4182.
41. (a) G. Natta, Angew. Chem., 1956, 68, 393;
42. (b) G. Natta, M. Peraldo and G. Allegra, Makromol. Chem., 1964, 75, 215.
43. R. W. Hoffmann, Angew. Chem., Int. Ed. Engl., 1992, 31, 1124.
44. For recent examples of conformational design, see: (a) R. Göttlich, B. Colin Kahrs, J. Krüger and R. W. Hoffmann, Chem. Commun., 1997, 247;
45. (b) U. Schöpfer, M. Stahl, T. Brandi and R. W. Hoffmann, Angew. Chem., Int. Ed. Engl., 1997, 36, 1745;
46. M. T. Burger, A. Armstrong, F. Guarnieri, D. Q. McDonald and W. C. Still, J. Am. Chem. Soc., 1994, 116, 3593.
47. F. Mohamadi, N. G. J. Richards, W C. Guida, R. Liskamp, M. Lipton, C. Caufield, G. Chang, T. Hendrickson and W. C. Still, J. Comput. Chem., 1990, 11, 440.
48. (a) C. A. G. Haasnoot, F. A. A. M. de Leeuw and C. Altona, Tetrahedron, 1980, 36, 2783;
49. (b) C. A. G. Haasnoot, F. A. A. M. de Leeuw, H. P. M. de Leeuw and C. Altona, Org. Afagn. Reson., 1981, 15, 43.
50. Evans and co-workers have developed a complementary approach to the aldol-based construction of polypropionates using their β-keto imide dipropionyl building block. See, for example: (a) D. A. Evans, A. S. Kim, R. Metternich and V. J. Novack, J. Am. Chem. Soc., 1998, 120, 5921;
51. (b) D. A. Evans, H. P. Ng, J. S. Clark and D. L. Rieger, Tetrahedron, 1992, 48, 2127;
52. D. A. Evans, J. S. Clark, R. Metternich, V. J. Novack and G. S. Sheppard, J. Am. Chem. Soc., 1990, 112, 866.