First enantioselective total synthesis of a naturally occurring dolabellane. Revision of absolute configuration

Journal of the American Chemical Society

Volumn 118, Issue 5, 1996, Pages 1229-1230

  Corey, E J ^a   Kania, Robert S ^a  

^a HARVARD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DITERPENOID; DOLABELLANE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOMER; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; NUCLEAR MAGNETIC RESONANCE;

EID: 0029928630     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9536779     Document Type: Article

References (33)

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7. For original literature on other members of the dolabellane family, see: (a) Ireland, C.; Faulkner, D. J.; Finer, J.; Clardy, J. J. Am. Chem. Soc. 1976, 98, 4664. (b) Tringali, C.; Piatelli, M.; Nicolosi, G. Tetrahedron 1984, 40, 799. (c) Rao, C. B.; Pullaiah, K. C.; Surapeneni, R. K.; Sullivan, B. W.; Albizati, K. F.; Faulkner, D. J.; Cun-heng, H.; Clardy, J. J. Org. Chem. 1986, 51, 2736. (d) Matsuo, A.; Yoshida, K.; Uohama, K.; Hayashi, S.; Connolly, J. D.; Sim, G. A. Chem. Lett. 1985, 935. (e) González, A. G.; Martín, J. D.; Norte, M.; Pérez, R.; Weyler, V.; Rafii, S.; Clardy, J. Tetrahedron Lett. 1983, 24, 1075. (f) Mori, K.; Iguchi, K.; Yamada, N.; Yamada, Y.; Inouye, Y. Tetrahedron Lett. 1987, 28, 5673. (g) Kobayashi, M.; Son, B. W.; Fujiwara, T.; Kyogoku, Y.; Kitagawa, I. Tetrahedron Lett. 1984, 25, 5543.
8. For original literature on other members of the dolabellane family, see: (a) Ireland, C.; Faulkner, D. J.; Finer, J.; Clardy, J. J. Am. Chem. Soc. 1976, 98, 4664. (b) Tringali, C.; Piatelli, M.; Nicolosi, G. Tetrahedron 1984, 40, 799. (c) Rao, C. B.; Pullaiah, K. C.; Surapeneni, R. K.; Sullivan, B. W.; Albizati, K. F.; Faulkner, D. J.; Cun-heng, H.; Clardy, J. J. Org. Chem. 1986, 51, 2736. (d) Matsuo, A.; Yoshida, K.; Uohama, K.; Hayashi, S.; Connolly, J. D.; Sim, G. A. Chem. Lett. 1985, 935. (e) González, A. G.; Martín, J. D.; Norte, M.; Pérez, R.; Weyler, V.; Rafii, S.; Clardy, J. Tetrahedron Lett. 1983, 24, 1075. (f) Mori, K.; Iguchi, K.; Yamada, N.; Yamada, Y.; Inouye, Y. Tetrahedron Lett. 1987, 28, 5673. (g) Kobayashi, M.; Son, B. W.; Fujiwara, T.; Kyogoku, Y.; Kitagawa, I. Tetrahedron Lett. 1984, 25, 5543.
9. For original literature on other members of the dolabellane family, see: (a) Ireland, C.; Faulkner, D. J.; Finer, J.; Clardy, J. J. Am. Chem. Soc. 1976, 98, 4664. (b) Tringali, C.; Piatelli, M.; Nicolosi, G. Tetrahedron 1984, 40, 799. (c) Rao, C. B.; Pullaiah, K. C.; Surapeneni, R. K.; Sullivan, B. W.; Albizati, K. F.; Faulkner, D. J.; Cun-heng, H.; Clardy, J. J. Org. Chem. 1986, 51, 2736. (d) Matsuo, A.; Yoshida, K.; Uohama, K.; Hayashi, S.; Connolly, J. D.; Sim, G. A. Chem. Lett. 1985, 935. (e) González, A. G.; Martín, J. D.; Norte, M.; Pérez, R.; Weyler, V.; Rafii, S.; Clardy, J. Tetrahedron Lett. 1983, 24, 1075. (f) Mori, K.; Iguchi, K.; Yamada, N.; Yamada, Y.; Inouye, Y. Tetrahedron Lett. 1987, 28, 5673. (g) Kobayashi, M.; Son, B. W.; Fujiwara, T.; Kyogoku, Y.; Kitagawa, I. Tetrahedron Lett. 1984, 25, 5543.
10. For original literature on other members of the dolabellane family, see: (a) Ireland, C.; Faulkner, D. J.; Finer, J.; Clardy, J. J. Am. Chem. Soc. 1976, 98, 4664. (b) Tringali, C.; Piatelli, M.; Nicolosi, G. Tetrahedron 1984, 40, 799. (c) Rao, C. B.; Pullaiah, K. C.; Surapeneni, R. K.; Sullivan, B. W.; Albizati, K. F.; Faulkner, D. J.; Cun-heng, H.; Clardy, J. J. Org. Chem. 1986, 51, 2736. (d) Matsuo, A.; Yoshida, K.; Uohama, K.; Hayashi, S.; Connolly, J. D.; Sim, G. A. Chem. Lett. 1985, 935. (e) González, A. G.; Martín, J. D.; Norte, M.; Pérez, R.; Weyler, V.; Rafii, S.; Clardy, J. Tetrahedron Lett. 1983, 24, 1075. (f) Mori, K.; Iguchi, K.; Yamada, N.; Yamada, Y.; Inouye, Y. Tetrahedron Lett. 1987, 28, 5673. (g) Kobayashi, M.; Son, B. W.; Fujiwara, T.; Kyogoku, Y.; Kitagawa, I. Tetrahedron Lett. 1984, 25, 5543.
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15. The tetr-butyldiphenylsilyl ether 2 was prepared in 99% yield by reaction in DMF of TBDPSC1 and imidazole with the corresponding bromo alcohol, which was made according to Corey et al.; Corey, E. J.; Bock, M. G.; Kozikowski, A. P.; Rama Rao, A. V.; Floyd, D.; Lipshutz. B. Tetrahedron Lett. 1978, 12, 1051.
16. 3OH. and (d) MsCl-LiCl (71% overall).
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20. 2BBr in enantioselective syn and anti aldol reactions, see: Corey, E. J.; Kim, S. S. J. Am. Chem. Soc. 1990, 112, 4976.
21. 2BBr reagent.
22. 1H NMR analysis. The enantiopurity of 9 was determined by HPLC analysis using a Chiralcel OD column (Chiral Technologies). Details may be found in the supporting information.
23. For a number of recent examples of non-enantioselective syntheses of medium rings from lactones by Claisen rearrangement. see: (a) Wipf. P. In Compr. Org. Synth. 1991. 5, 827 (review). (b) Magriotis, P. A.; Kim, K. D. J. Am. Chem. Soc. 1993, 115, 2972. (c) Abelman, M. M.; Funk, R. L.; Munger, J. D., Jr. J. Am. Chem. Soc. 1982, 104. 4030. (d) Knight, D. W.; Cameron, A. G. Tetrahedron Lett. 1982, 51, 5455.
24. For a number of recent examples of non-enantioselective syntheses of medium rings from lactones by Claisen rearrangement. see: (a) Wipf. P. In Compr. Org. Synth. 1991. 5, 827 (review). (b) Magriotis, P. A.; Kim, K. D. J. Am. Chem. Soc. 1993, 115, 2972. (c) Abelman, M. M.; Funk, R. L.; Munger, J. D., Jr. J. Am. Chem. Soc. 1982, 104. 4030. (d) Knight, D. W.; Cameron, A. G. Tetrahedron Lett. 1982, 51, 5455.
25. For a number of recent examples of non-enantioselective syntheses of medium rings from lactones by Claisen rearrangement. see: (a) Wipf. P. In Compr. Org. Synth. 1991. 5, 827 (review). (b) Magriotis, P. A.; Kim, K. D. J. Am. Chem. Soc. 1993, 115, 2972. (c) Abelman, M. M.; Funk, R. L.; Munger, J. D., Jr. J. Am. Chem. Soc. 1982, 104. 4030. (d) Knight, D. W.; Cameron, A. G. Tetrahedron Lett. 1982, 51, 5455.
26. For a number of recent examples of non-enantioselective syntheses of medium rings from lactones by Claisen rearrangement. see: (a) Wipf. P. In Compr. Org. Synth. 1991. 5, 827 (review). (b) Magriotis, P. A.; Kim, K. D. J. Am. Chem. Soc. 1993, 115, 2972. (c) Abelman, M. M.; Funk, R. L.; Munger, J. D., Jr. J. Am. Chem. Soc. 1982, 104. 4030. (d) Knight, D. W.; Cameron, A. G. Tetrahedron Lett. 1982, 51, 5455.
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32. 13C NMR. UV. IR. and MS data obtained for synthetic 1 were identical with those obtained for natural dolabellatrienone. We are grateful to Dr. William Fenical for providing copies of the spectra of natural 1.
33. Detailed X-ray crystallographic data are available from the Cambridge Crystallographic Data Centre. 12 Union Road. Cambridge. CB2 1EZ. U.K.