Enantioselective synthesis of the [6,6] spiroketal core of reveromycin A

Organic Letters

Volumn 2, Issue 2, 2000, Pages 207-210

  Drouet, Keith E ^a   Ling, Taotao ^a   Tran, Hung V ^a   Theodorakis, Emmanuel A ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC AGENT; EPIDERMAL GROWTH FACTOR; PROTEIN SYNTHESIS INHIBITOR; PYRAN DERIVATIVE; REVEROMYCIN A; SPIRO COMPOUND;

ARTICLE; CHEMISTRY; DRUG ANTAGONISM; NUCLEAR MAGNETIC RESONANCE; STEREOISOMERISM; STREPTOMYCES; SYNTHESIS;

ANTINEOPLASTIC AGENTS; EPIDERMAL GROWTH FACTOR; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; PROTEIN SYNTHESIS INHIBITORS; PYRANS; SPIRO COMPOUNDS; STEREOISOMERISM; STREPTOMYCES;

EID: 0034719268     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol991290v     Document Type: Article

References (39)

1. (a) Takahashi, H.; Osada, H.; Koshino, H.; Sasaki, M.; Onose, R.; Nakakoshi, M.; Yoshihama, M.; Isono, K. J. Antibiot. 1992, 45, 1414-1419.
2. (b) Takahashi, H.; Yamashita, Y.; Takaoka, H.; Nakamura, J.; Yoshihama, M.; Osada, H. Oncology Res. 1997, 9, 7-11.
3. (c) Osada, H.; Koshino, H.; Isono, K.; Takahashi, H.; Kawanishi, G. J. Antibiot. 1991, 44, 259-261.
4. (a) Takahashi, H.; Osada, H.; Koshino, H.; Kudo, T.; Amano, S.; Shimizu, S.; Yoshihama, M.; Isono, K. J. Antibiot. 1992, 45, 1409-1413.
5. (b) Koshino, H.; Takahashi, H.; Osada, H.; Isono, K. J. Antibiot. 1992, 45, 1420-1427.
6. (c) Ubukata, M.; Koshino, H.; Osada, H.; Isono, K. J. Chem. Soc., Chem. Commun. 1994, 1877-1878.
7. For recent reviews on EGF receptor, see: Growth Factors and Receptors: a Practical Approach: McCay, I. A., Brown, K. D., Eds.; University Press: New York, 1998. Growth Factors and Signal Transduction in Development; Nilsen-Hamilton, M., Ed.; Wiley-Liss: New York, 1994.
8. For recent reviews on EGF receptor, see: Growth Factors and Receptors: a Practical Approach: McCay, I. A., Brown, K. D., Eds.; University Press: New York, 1998. Growth Factors and Signal Transduction in Development; Nilsen-Hamilton, M., Ed.; Wiley-Liss: New York, 1994.
9. For selected references on the importance of EGF receptor in anticancer drug design, see: Stearns, M. E.; Stearns, M. Cancer Metastasis Rev. 1993, 12, 39-52. Klijn, J. G. M.; Berns, P. M. J. J.; Schmitz, P. I. M.; Foekens, J. A. Endocrine Rev. 1992, 13, 3-17. Modjtahedi, H.; Dean, C. Intern. J. Oncol. 1994, 4, 277-296.
10. For selected references on the importance of EGF receptor in anticancer drug design, see: Stearns, M. E.; Stearns, M. Cancer Metastasis Rev. 1993, 12, 39-52. Klijn, J. G. M.; Berns, P. M. J. J.; Schmitz, P. I. M.; Foekens, J. A. Endocrine Rev. 1992, 13, 3-17. Modjtahedi, H.; Dean, C. Intern. J. Oncol. 1994, 4, 277-296.
11. For selected references on the importance of EGF receptor in anticancer drug design, see: Stearns, M. E.; Stearns, M. Cancer Metastasis Rev. 1993, 12, 39-52. Klijn, J. G. M.; Berns, P. M. J. J.; Schmitz, P. I. M.; Foekens, J. A. Endocrine Rev. 1992, 13, 3-17. Modjtahedi, H.; Dean, C. Intern. J. Oncol. 1994, 4, 277-296.
12. Drouet, K. E.; Theodorakis, E. A. J. Am. Chem. Soc. 1999, 121, 456-457.
13. Masuda, T.; Osako, K.; Shimizu, T.; Nakata, T. Org. Lett. 1999, 1, 941-944.
14. (a) Shimizu, T.; Kobayashi, R.; Osako, K.; Osada, H.; Nakata, T. Tetrahedron Lett. 1996, 37, 6755-6758.
15. (b) McRae, K. J.; Rizzacasa, M. A. J. Org. Chem. 1997, 62, 1196-1197.
16. For a recent review on spiroketals, see: Perron, F.; Albizati, K. F. Chem. Rev. 1989, 89, 1617-1661.
17. The synthesis of iodide 7 is presented in the Supporting Information.
18. Andrews, G. C.; Crawford, T. C.; Bacon, B. E. J. Org. Chem. 1981, 46, 2976. Schmid, C. R,; Bradley, D. A. Synthesis 1992, 587-590.
19. Andrews, G. C.; Crawford, T. C.; Bacon, B. E. J. Org. Chem. 1981, 46, 2976. Schmid, C. R,; Bradley, D. A. Synthesis 1992, 587-590.
20. Heathcock, C. H.; Young, S. D.; Hagen, J. P.; Pirrung, M. C.; White, C. T.; vanDerveer, D. J. Org. Chem. 1980, 45, 3846-3856. Nagano, H.; Ohno, M.; Miyamae, Y.; Kuno, Y. Bull. Chem. Soc. Jpn. 1992, 65, 5, 2814-2820. Nagano, H.; Ohno, M.; Miyamae, Y. Chem. Lett. 1990, 463-466. Still, W. C.; McDonald, J. H. Tetrahedron Lett. 1980, 21, 1031-1034. Still, W. C.; Schneider J. A. Tetrahedron Lett. 1980, 21, 1035-1038.
21. Heathcock, C. H.; Young, S. D.; Hagen, J. P.; Pirrung, M. C.; White, C. T.; vanDerveer, D. J. Org. Chem. 1980, 45, 3846-3856. Nagano, H.; Ohno, M.; Miyamae, Y.; Kuno, Y. Bull. Chem. Soc. Jpn. 1992, 65, 5, 2814-2820. Nagano, H.; Ohno, M.; Miyamae, Y. Chem. Lett. 1990, 463-466. Still, W. C.; McDonald, J. H. Tetrahedron Lett. 1980, 21, 1031-1034. Still, W. C.; Schneider J. A. Tetrahedron Lett. 1980, 21, 1035-1038.
22. Heathcock, C. H.; Young, S. D.; Hagen, J. P.; Pirrung, M. C.; White, C. T.; vanDerveer, D. J. Org. Chem. 1980, 45, 3846-3856. Nagano, H.; Ohno, M.; Miyamae, Y.; Kuno, Y. Bull. Chem. Soc. Jpn. 1992, 65, 5, 2814-2820. Nagano, H.; Ohno, M.; Miyamae, Y. Chem. Lett. 1990, 463-466. Still, W. C.; McDonald, J. H. Tetrahedron Lett. 1980, 21, 1031-1034. Still, W. C.; Schneider J. A. Tetrahedron Lett. 1980, 21, 1035-1038.
23. Heathcock, C. H.; Young, S. D.; Hagen, J. P.; Pirrung, M. C.; White, C. T.; vanDerveer, D. J. Org. Chem. 1980, 45, 3846-3856. Nagano, H.; Ohno, M.; Miyamae, Y.; Kuno, Y. Bull. Chem. Soc. Jpn. 1992, 65, 5, 2814-2820. Nagano, H.; Ohno, M.; Miyamae, Y. Chem. Lett. 1990, 463-466. Still, W. C.; McDonald, J. H. Tetrahedron Lett. 1980, 21, 1031-1034. Still, W. C.; Schneider J. A. Tetrahedron Lett. 1980, 21, 1035-1038.
24. Heathcock, C. H.; Young, S. D.; Hagen, J. P.; Pirrung, M. C.; White, C. T.; vanDerveer, D. J. Org. Chem. 1980, 45, 3846-3856. Nagano, H.; Ohno, M.; Miyamae, Y.; Kuno, Y. Bull. Chem. Soc. Jpn. 1992, 65, 5, 2814-2820. Nagano, H.; Ohno, M.; Miyamae, Y. Chem. Lett. 1990, 463-466. Still, W. C.; McDonald, J. H. Tetrahedron Lett. 1980, 21, 1031-1034. Still, W. C.; Schneider J. A. Tetrahedron Lett. 1980, 21, 1035-1038.
25. All new compounds exhibited satisfactory spectral and analytical data (see Supporting Information).
26. For selected reviews on this topic, see: Jurczak, J.; Pikul, S.; Bauer, T. Tetrahedron 1986, 42, 447-488. Reetz, M. T. Acc. Chem. Res. 1993, 26, 462-468. Reetz, M. T. Angew. Chem., Int. Ed. Engl. 1984, 23, 556-569.
27. For selected reviews on this topic, see: Jurczak, J.; Pikul, S.; Bauer, T. Tetrahedron 1986, 42, 447-488. Reetz, M. T. Acc. Chem. Res. 1993, 26, 462-468. Reetz, M. T. Angew. Chem., Int. Ed. Engl. 1984, 23, 556-569.
28. For selected reviews on this topic, see: Jurczak, J.; Pikul, S.; Bauer, T. Tetrahedron 1986, 42, 447-488. Reetz, M. T. Acc. Chem. Res. 1993, 26, 462-468. Reetz, M. T. Angew. Chem., Int. Ed. Engl. 1984, 23, 556-569.
29. Corey, E. J.; Fuchs, P. L. Tetrahedron Lett. 1972, 3769-3772.
30. Humphrey, J. M.; Eggen, J. B.; Chamberlin, A. R. J. Am. Chem. Soc. 1996, 118, 11759-11770. Cliff, M. D.; Pyne, S. G. J. Org. Chem. 1997, 62, 1023-1032.
31. Humphrey, J. M.; Eggen, J. B.; Chamberlin, A. R. J. Am. Chem. Soc. 1996, 118, 11759-11770. Cliff, M. D.; Pyne, S. G. J. Org. Chem. 1997, 62, 1023-1032.
32. Dess, D. B.; Martin, J. C. J. Am. Chem. Soc. 1991, 113, 7277-7287. Ireland, R. E.; Liu, L. J. Org. Chem. 1993, 58, 2899.
33. Dess, D. B.; Martin, J. C. J. Am. Chem. Soc. 1991, 113, 7277-7287. Ireland, R. E.; Liu, L. J. Org. Chem. 1993, 58, 2899.
34. Ireland, R. E.; Daub, J. P. J. Org. Chem. 1983, 48, 1303-1312. Baker, R.; Herbert, R. H.; Patron, A. H. J. Chem. Soc., Chem. Commun. 1982, 601-604.
35. Ireland, R. E.; Daub, J. P. J. Org. Chem. 1983, 48, 1303-1312. Baker, R.; Herbert, R. H.; Patron, A. H. J. Chem. Soc., Chem. Commun. 1982, 601-604.
36. We thank the referees for this comment.
37. Deslongchamps, P.; Rowan, D. D.; Pothier, N.; Sauve, T.; Saunders: J. K. Can. J. Chem. 1981, 59, 1105-1121. Evans, D. A.; Sacks, C. E.; Kleschick, W. A.; Taber, T. R. J. Am. Chem. Soc. 1979, 101, 6789-6791.
38. Deslongchamps, P.; Rowan, D. D.; Pothier, N.; Sauve, T.; Saunders: J. K. Can. J. Chem. 1981, 59, 1105-1121. Evans, D. A.; Sacks, C. E.; Kleschick, W. A.; Taber, T. R. J. Am. Chem. Soc. 1979, 101, 6789-6791.
39. Computational studies were performed using MM2 calculations with CS Chem3D Pro. See Supporting Information for more details.