Asymmetric synthesis of the northern half C1-C16 of the bryostatins

Organic Letters

Volumn 3, Issue 6, 2001, Pages 929-932

  Vakalopoulos, A ^a   Lampe, T F J ^a   Hoffmann, H M R ^a  

^a LEIBNIZ UNIVERSITY HANNOVER   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC AGENT; BRYOSTATIN 1; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; LACTONE; MACROLIDE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; SYNTHESIS;

ANTINEOPLASTIC AGENTS; INDICATORS AND REAGENTS; LACTONES; MACROLIDES; MODELS, MOLECULAR; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE;

EID: 0035932595     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol015551o     Document Type: Article

References (48)

1. (a) Pettit, G. R. J. Nat. Prod. 1996, 59, 812.
2. (b) Pettit, G. R. The Bryostatins. In Progress in the Chemisty of Organic Natural Products; Herz, W., Ed.; Springer-Verlag: New York, 1991; Vol. 57, p 153.
3. (a) Kraft, A. S. Natl. Cancer Inst. 1993, 85, 1790.
4. (b) Stone, R. M. Leukemia Res. 1997, 21, 399.
5. (c) Schuchter, L. M.; Esa, A. H.; May, W.; Laulis, M. K.; Pettit, G. R.; Hess, A. D. Cancer Res. 1991, 51, 682.
6. Information on the status of bryostatin clinical trials can be found via the Internet at http://cancernet.nci.nih.gov/prot/protsrch.shtml.
7. (a) Kageyama, M.; Tamura, T.; Nantz, M. H.; Roberts, J. C.; Somfai, P.; Whritenour, D. C.; Masamune, S. J. J. Am. Chem. Soc. 1990, 112, 7407 and references therein.
8. (b) Evans, D. A.; Carter, P. H.; Carreira, E. M.; Charette, A. B.; Prunet, J. A.; Lautens, M. J. Am. Chem. Soc. 1999, 121, 7540 and references therein.
9. (c) Ohmori, K.; Ogawa, Y.; Obitsu, T.; Ishikawa, Y.; Nishiyama, S.; Yamamura, S. Angew. Chem. 2000, 112, 2376; Angew. Chem., Int. Ed. 2000, 39, 2290 and references therein.
10. (c) Ohmori, K.; Ogawa, Y.; Obitsu, T.; Ishikawa, Y.; Nishiyama, S.; Yamamura, S. Angew. Chem. 2000, 112, 2376; Angew. Chem., Int. Ed. 2000, 39, 2290 and references therein.
11. Other segment syntheses: (a) Almendros, P.; Rae, A.; Thomas, E. J. Tetrahedron Lett. 2000, 41, 9565.
12. (b) Hale, K. J.; Hummersone, M. G.; Bhatia G. S. Org. Lett. 2000, 2, 2189.
13. (c) Baxter, J.; Mata, E. G.; Thomas, E. J. Tetrahedron 1998, 54, 14359.
14. (d) Gracia, J.; Thomas, E. J. J. Chem. Soc., Perkin Trans I 1998, 2865.
15. (e) Maguire, R. J.; Munt, S. P.; Thomas, E. J. J. Chem Soc., Perkin Trans. I 1998, 2853.
16. (f) Kiyooka, S.; Maeda, H. Tetrahedron: Asymmetry 1997, 8, 3371.
17. (g) De Brabander, J.; Kulkarni, A.; Garcia-Lopez, R.; Vandewalle, M. Tetrahedron: Asymmetry 1997, 8, 1721.
18. (h) Kalesse, M.; Eh, M. Tetrahedron Lett. 1996, 37, 1767.
19. (i) De Brabander, J.; Vandewalle, M. Pure Appl. Chem. 1996, 68, 715.
20. (j) Hoffmann, R. W.; Stiasny, H. C. Tetrahedron Lett. 1995, 36, 4595. Detailed review of the literature prior to early 1995.
21. (k) Norcross, R. D.; Paterson, I. Chem. Rev. 1995, 95, 2041-2114.
22. (a) Lampe, T. F. J.; Hoffmann, H. M. R. Tetrahedron Lett. 1996, 37, 7695.
23. (b) Lampe, T. F. J.; Hoffmann, H. M. R. J. Chem. Soc., Chem. Commun. 1996, 1931.
24. (c) Weiss, J. M.; Hoffmann, H. M. R. Tetrahedron: Asymmetry 1997, 8, 3913.
25. (a) Wender, P. A.; De Brabander, J.; Harran, P. G.; Jimenez, J.-M.; Koehler, M. F. T.; Lippa, B.; Park, C.-M.; Shiozaki, M. J. Am. Chem. Soc. 1998, 120, 4534.
26. (b) Wender, P. A.; De Brabander, J.; Harran, P. G.; Hinkle, K. W.; Lippa, B.; Pettit, G. R. Tetrahedron Lett. 1998, 39, 8625.
27. (c) Wender, P. A.; Lippa, B. Tetrahedron Lett. 2000, 41, 1007.
28. (d) Wender, P. A.; Hinkle, K. W. Tetrahedron Lett. 2000, 41, 6725.
29. (a) Föhlisch. B.: Herter, R. Synthesis 1982, 976.
30. (b) Hoffmann, H. M. R.; Clemens, K. E.; Smithers, R. H. J. Am. Chem. Soc. 1972, 94, 3940. Hoffmann, H. M. R.; Iqbal, M. N. Tetrahedron Lett. 1975, 16, 4487.
31. (b) Hoffmann, H. M. R.; Clemens, K. E.; Smithers, R. H. J. Am. Chem. Soc. 1972, 94, 3940. Hoffmann, H. M. R.; Iqbal, M. N. Tetrahedron Lett. 1975, 16, 4487.
32. Brown, H. C.; Joshi, N. N. J. Org. Chem. 1988, 53, 4059 and references therein.
33. For a detailed consideration of the opening of methoxy acetals, see: Vakalopoulos, A.; Hoffmann, H. M. R. Org. Lett. 2001, 3, 111.
34. (a) Saksena, A. K.; Mangiaracina, P. Tetrahedron Lett. 1983, 24, 273.
35. (b) Evans, D. A.; Chapman, K. T.; Carreira, E. M. J. Am. Chem. Soc. 1988, 110, 3560.
36. Freeman, P. K.; Hutchinson, L. L. J. Org. Chem. 1980, 45, 1924.
37. Lampe, T. F. J.; Hoffmann, H. M. R.; Bornscheuer, U. T. Tetrahedron: Asymmetry 1996, 7, 2889.
38. For further enzymatic desymmetrization of related tetrahydropyrans, see: Chênevert, R.; Goupil, D.; Rose, Y. S.; Bédard, E. Tetrahedron: Asymmetry 1998, 9, 4285.
39. Lampe, T. F. J.; Hoffmann, H. M. R. J. Chem. Soc., Chem. Commun. 1996, 2637.
40. 2P-(O)H: Froneman, M.; Modro, T. A. Tetrahedron Lett. 1988, 29, 3327.
41. 2i-Pr. Ye, W.; Liao, X. Synthesis 1985, 986.
42. Smith, A. B.; Condon, S. M.; McCauley, J. A. Acc. Chem. Res. 1998, 31, 35. Seebach, D. Angew. Chem., Int. Ed. Engl. 1969, 8, 639.
43. Smith, A. B.; Condon, S. M.; McCauley, J. A. Acc. Chem. Res. 1998, 31, 35. Seebach, D. Angew. Chem., Int. Ed. Engl. 1969, 8, 639.
44. (a) Hayward, C. M.; Yohannes, D.; Danishefsky, S. J. J. Am. Chem. Soc. 1993, 115, 9345.
45. (b) Smith, A. B.; Chen, S. S.-Y.; Nelson, F. C.; Reichert, J. M.; Salvatore, B. A. J. Am. Chem. Soc. 1997, 119, 10935.
46. (a) Brief survey: Misske, A. M.; Hoffmann, H. M. R. Chem. Eur. J. 2000, 6, 3313 and literature therein.
47. (b) Reference 10.
48. Vakalopoulos, A.; Hoffmann, H. M. R. Org. Lett. 2000, 2, 1447.