Solving a synthetic puzzle

Chemistry and Industry (London)

Volumn , Issue 2, 2000, Pages 59-65

  Hepworth, David ^a  

^a PFIZER GLOBAL RESEARCH AND DEVELOPMENT   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

NATURALLY OCCURRING; POTENTIAL DRUG;

EID: 0042829604     PISSN: 00093068     EISSN: None     Source Type: Trade Journal    
DOI: None     Document Type: Article

References (42)

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2. Nicolaou, K.C. & Sorensen, E.J., in 'Classics in total synthesis', Weinheim: VCH, 1996, 10
3. a (a) Dabrah, T.T., Harwood Jr, H.J., Huang, L.H. & Kaneko, T., US Patent No. 5430055;
4. (b) Dabrah, T.T., et at. J. Antibiotics, 1997, 50, 1-7
5. The name is derived from the producing organism (a 'Phomaoid' fungus) and the relation of these molecules to the nonadrides (see ref 9)
6. The fungus is thought to be of the Phoma species see ref 3a
7. Nicolaou, K.C. & Nadin, A., Angew. Chem. Int. Ed. Engl., 1996, 35, 1622-56
8. Dabrah, T.T., Kaneko, T., Massefski Jr, W. & Whipple, E.B., J. Am. Chem. Soc., 1997, 119, 1594-8
9. (a) Köbrich, G., Angew. Chem. Int. Ed. Engl., 1973, 12, 464-73;
10. (b) Buchannan, G.L., Chem. Soc. Rev., 1974, 3, 41-63;
11. (c) Shea, K.L., Tetrahedron, 1980, 36, 1683-1715
12. Barton, D.H.R. & Sutherland, J.K., J. Chem. Soc., 1965, 1769-72, and subsequent three papers
13. Spencer, P., Agnelli, F., Williams, H.J., Keller, N.P. & Sulikowski, G.A., J. Am. Chem. Soc., 2000. in press
14. (a)Nicolaou, K.C., et al, Angew. Chem. Int. Ed., 1999, 38, 1669-75:
15. (b) Nicolaou, K.C., et al. Angew. Chem. Int. Ed., 1999, 38, 1676-8
16. Nicolaou, K.C., Härter, M.W., Boulton, L. & Jandeleit, B., Angew. Chem., Int. Ed. Engl., 1991, 36, 1194-6
17. Waizumi, N., Itoh, T. & Fukuyama, T., Tetrahedron Lett., 1998, 39, 6015-18
18. Nicolaou, K.C., Postema, M.H.D., Miller, N.D. & Yang, G., Angew. Chem. Int. Ed. Engl., 1997, 36, 2821-3
19. An earlier attempt to use a similar reaction sequence for the synthesis of models of the CP-molecules provided only circumstantial evidence for the success of the divinylcyclopropane rearrangement; Davies, H.M.L., Calvo, R. & Ahmed, G., Tetrahedron Lett., 1997, 38, 1737-40
20. Armstrong, A., Critchley, T.J. & Mortlock, A.A., Synlett, 1998, 552-3
21. Bio, M.M. & Leighton, J.L., J. Am. Chem. Soc., 1999, 121, 890-1
22. Sgarbi, P.W.M. & Clive, D.L.J., Chem. Commun., 1997, 2157-8. For a recent disclosure of more advanced model systems along these lines see: Clive, D.L.J., Sun, S., He, X., Zhang, J. & Gagliardini, V., Tetrahedron Lett., 1999, 40, 4605-9; Clive, D.L.J. & Zhang, J., Tetrahedron, 1999, 55, 12059-68
23. Sgarbi, P.W.M. & Clive, D.L.J., Chem. Commun., 1997, 2157-8. For a recent disclosure of more advanced model systems along these lines see: Clive, D.L.J., Sun, S., He, X., Zhang, J. & Gagliardini, V., Tetrahedron Lett., 1999, 40, 4605-9; Clive, D.L.J. & Zhang, J., Tetrahedron, 1999, 55, 12059-68
24. Sgarbi, P.W.M. & Clive, D.L.J., Chem. Commun., 1997, 2157-8. For a recent disclosure of more advanced model systems along these lines see: Clive, D.L.J., Sun, S., He, X., Zhang, J. & Gagliardini, V., Tetrahedron Lett., 1999, 40, 4605-9; Clive, D.L.J. & Zhang, J., Tetrahedron, 1999, 55, 12059-68
25. Chen, C., Layton, M.E. & Shair, M.D., J. Am. Chem. Soc., 1998, 120, 10784-5
26. Kwon, O., Su, D.-S., Meng, D., Deng, W., D'Amico, D.C. & Danishefsky, S.J., Angew. Chem. Int. Ed., 1998, 37, 1877-80
27. For other work from this group providing access to primitive CP-model systems see: Frontier, A.J., Danishefsky, S.J., Koppel, G.A. & Meng, D., Tetrahedron, 1998, 54, 12721-36
28. Kwon, O., Su, D.-S., Meng, D., Deng, W., D'Amico, D.C. & Danishefsky, S.J., Angew. Chem. Int. Ed., 1998, 37, 1880-2
29. Meng, D. & Danishefsky, S.J., ibid, 1999, 38, 1485-8
30. Meng, D., Tan, Q. & Danishefsky, S.J., ibid, 1999, 38, 3197-201
31. Nicolaou, K.C., et al, ibid, 1999, 38, 549-52
32. See ref 25 for a more in -depth mechanistic analysis
33. Nicolaou, K.C., et al, Org. Lett., 1999, 1, 63-6
34. Nicolaou, K.C., et al, ibid. 1999, 1, 883-6
35. The side reaction has led to the discovery of new synthetic methodology, see: Nicolaou, K.C., et al, Angew. Chem. Int. Ed., 2000, in press
36. See ref 11b for a full mechanistic rationale
37. Watson, N.S. & Procopiou, P.A., Prog. Med. Chem., 1996, 33, 331-78
38. For a review see: Hinterding, K., Alonso-Diaz, D. & Waldmann, H., Angew. Chem. Int. Ed., 1998, 37, 688-749
39. For reviews see: (a) Qian, Y. Sebti, S.M. & Hamilton, A.D., Biopolymers, 1997, 43, 25-41:
40. (b) Gibbs, J.B., et al, Curr. Opin. Chem. Biol., 1997, 1, 197-203:
41. (c) Yang, W., Villar, K.D., Urano, J., Mitsuzawa, H. & Tamanoi, F., J. Cell. Biochem., 1997, 67, 12-19;
42. (d) Buss, J.E. & Marsters Jr, J.C., Chem. Biol., 1995, 2, 787-91