Enantiocontrolled Synthesis of Jasmonates via Tandem Retro-Diels-Alder-Ene Reaction Activated by a Silyl Substituent

Organic Letters

Volumn 6, Issue 3, 2004, Pages 409-411

  Suzuki, Katsufumi ^a   Inomata, Kohei ^a   Endo, Yasuyuki ^a  

^a TOHOKU PHARMACEUTICAL UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

JASMONIC ACID; LACTONE DERIVATIVE; METHYL GROUP; SILANE DERIVATIVE;

ARTICLE; CHIRALITY; DIELS ALDER REACTION; ENANTIOSELECTIVITY;

CYCLOPENTANES; LACTAMS; MOLECULAR STRUCTURE; PLANT GROWTH REGULATORS; STEREOISOMERISM;

EID: 1342264148     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol036253p     Document Type: Article

References (34)

1. (a) Suzuki, K.; Shoji, M.; Kobayashi, E.; Inomata, K. Tetrahedron: Asymmetry 2001, 12, 2789.
2. (b) Suzuki, K.; Inomata, K. Tetrahedron Lett. 2003, 44, 745.
3. (c) Suzuki, K.; Inomata, K,; Endo, Y. Heterocycles 2003, 60, 2743.
4. Recent reviews for tandem reaction: (a) Ziegler, F. E. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press, Oxford, 1991; Vol. 5, p 875. (b) Tietze, L. F.; Beifuss, U. Angew. Chem., Int. Ed. Engl. 1993, 32, 131. (c) Bunce, R. A. Tetrahedron 1995, 51, 13103. (d) Parsons, P. J.; Penkett, C. S.; Shell, A. J. Chem. Rev. 1996, 96, 195. (e) Nicolaou, K. C.; Montagnon, T.; Snyder, S. A. Chem. Commun. 2003, 551.
5. Recent reviews for tandem reaction: (a) Ziegler, F. E. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press, Oxford, 1991; Vol. 5, p 875. (b) Tietze, L. F.; Beifuss, U. Angew. Chem., Int. Ed. Engl. 1993, 32, 131. (c) Bunce, R. A. Tetrahedron 1995, 51, 13103. (d) Parsons, P. J.; Penkett, C. S.; Shell, A. J. Chem. Rev. 1996, 96, 195. (e) Nicolaou, K. C.; Montagnon, T.; Snyder, S. A. Chem. Commun. 2003, 551.
6. Recent reviews for tandem reaction: (a) Ziegler, F. E. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press, Oxford, 1991; Vol. 5, p 875. (b) Tietze, L. F.; Beifuss, U. Angew. Chem., Int. Ed. Engl. 1993, 32, 131. (c) Bunce, R. A. Tetrahedron 1995, 51, 13103. (d) Parsons, P. J.; Penkett, C. S.; Shell, A. J. Chem. Rev. 1996, 96, 195. (e) Nicolaou, K. C.; Montagnon, T.; Snyder, S. A. Chem. Commun. 2003, 551.
7. Recent reviews for tandem reaction: (a) Ziegler, F. E. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press, Oxford, 1991; Vol. 5, p 875. (b) Tietze, L. F.; Beifuss, U. Angew. Chem., Int. Ed. Engl. 1993, 32, 131. (c) Bunce, R. A. Tetrahedron 1995, 51, 13103. (d) Parsons, P. J.; Penkett, C. S.; Shell, A. J. Chem. Rev. 1996, 96, 195. (e) Nicolaou, K. C.; Montagnon, T.; Snyder, S. A. Chem. Commun. 2003, 551.
8. Recent reviews for tandem reaction: (a) Ziegler, F. E. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press, Oxford, 1991; Vol. 5, p 875. (b) Tietze, L. F.; Beifuss, U. Angew. Chem., Int. Ed. Engl. 1993, 32, 131. (c) Bunce, R. A. Tetrahedron 1995, 51, 13103. (d) Parsons, P. J.; Penkett, C. S.; Shell, A. J. Chem. Rev. 1996, 96, 195. (e) Nicolaou, K. C.; Montagnon, T.; Snyder, S. A. Chem. Commun. 2003, 551.
9. Some examples of RDAE reaction: (a) Nakada, Y.; Sugahara, T.; Ogasawara, K. Tetrahedron Lett. 1997, 38, 857. (b) Nakagawa, H.; Sugahara, T.; Ogasawara, K. Tetrahedron Lett. 2001, 42, 4523.
10. Some examples of RDAE reaction: (a) Nakada, Y.; Sugahara, T.; Ogasawara, K. Tetrahedron Lett. 1997, 38, 857. (b) Nakagawa, H.; Sugahara, T.; Ogasawara, K. Tetrahedron Lett. 2001, 42, 4523.
11. Recent preparations of methyl 6-epi-cucurbate: (a) Helmchen, G.; Goeke, A.; Lauer, G.; Urmann, M.; Fries, J. Angew. Chem., Int. Ed. Engl. 1990, 29, 1024. (b) Kitahara, T.; Warita, Y.; Abe, M.; Seya, M.; Takagi, Y.; Mori, K. Agric. Biol. Chem. 1991, 55, 1013. (c) Kitahara, T.; Nishi, T.; Mori, K. Tetrahedron 1991, 47, 6999. (d) Dathe, W.; Schindler, C.; Schneider, G.; Schmidt, J.; Porzel, A.; Jensen, E.; Yamaguchi, I. Phytochemistry 1991, 30, 1909.
12. Recent preparations of methyl 6-epi-cucurbate: (a) Helmchen, G.; Goeke, A.; Lauer, G.; Urmann, M.; Fries, J. Angew. Chem., Int. Ed. Engl. 1990, 29, 1024. (b) Kitahara, T.; Warita, Y.; Abe, M.; Seya, M.; Takagi, Y.; Mori, K. Agric. Biol. Chem. 1991, 55, 1013. (c) Kitahara, T.; Nishi, T.; Mori, K. Tetrahedron 1991, 47, 6999. (d) Dathe, W.; Schindler, C.; Schneider, G.; Schmidt, J.; Porzel, A.; Jensen, E.; Yamaguchi, I. Phytochemistry 1991, 30, 1909.
13. Recent preparations of methyl 6-epi-cucurbate: (a) Helmchen, G.; Goeke, A.; Lauer, G.; Urmann, M.; Fries, J. Angew. Chem., Int. Ed. Engl. 1990, 29, 1024. (b) Kitahara, T.; Warita, Y.; Abe, M.; Seya, M.; Takagi, Y.; Mori, K. Agric. Biol. Chem. 1991, 55, 1013. (c) Kitahara, T.; Nishi, T.; Mori, K. Tetrahedron 1991, 47, 6999. (d) Dathe, W.; Schindler, C.; Schneider, G.; Schmidt, J.; Porzel, A.; Jensen, E.; Yamaguchi, I. Phytochemistry 1991, 30, 1909.
14. Recent preparations of methyl 6-epi-cucurbate: (a) Helmchen, G.; Goeke, A.; Lauer, G.; Urmann, M.; Fries, J. Angew. Chem., Int. Ed. Engl. 1990, 29, 1024. (b) Kitahara, T.; Warita, Y.; Abe, M.; Seya, M.; Takagi, Y.; Mori, K. Agric. Biol. Chem. 1991, 55, 1013. (c) Kitahara, T.; Nishi, T.; Mori, K. Tetrahedron 1991, 47, 6999. (d) Dathe, W.; Schindler, C.; Schneider, G.; Schmidt, J.; Porzel, A.; Jensen, E.; Yamaguchi, I. Phytochemistry 1991, 30, 1909.
15. Some selected chiral syntheses of methyl jasmonate: (a) Montforts, F.-P. ; Gesing-Zibulak, I.; Grammenos, W. Helv. Chim. Acta. 1989, 72, 1852. (b) Kiyota, H.; Higashi, E.; Koike, T.; Oritani, T. Tetrahedron: Asymmetry 2001, 12, 1035.
16. Some selected chiral syntheses of methyl jasmonate: (a) Montforts, F.-P. ; Gesing-Zibulak, I.; Grammenos, W. Helv. Chim. Acta. 1989, 72, 1852. (b) Kiyota, H.; Higashi, E.; Koike, T.; Oritani, T. Tetrahedron: Asymmetry 2001, 12, 1035.
17. Review: Beale, M. H.; Ward, J. L. Nat. Prod. Rep. 1998, 15, 533.
18. Seto, H.; Nomura, E.; Fujioka, S.; Koshino, H.; Suenaga, T.; Yoshida, S. Biosci. Biotechnol. Biochem. 1999, 63, 361.
19. Suzuki, K.; Inomata. K. Synthesis 2002, 1819.
20. Salomon, R. G.; Coughlin, D. J.; Ghosh, S.; Zagorski, M. G. J. Am. Chem. Soc. 1982, 104, 998.
21. (a) McCormick, J. P.; Barton, D. L. J. Org. Chem. 1980, 45, 2566.
22. (b) Ferreri, C.; Ambrosone, M. Synth. Commun. 1995, 25, 3351. Since (E)-5-bromopent-2-ene reported by these authors included ca. 10% of (Z)-isomer, the obtained diol 2b contained a trace amount of 2a, formed by the reaction with the (Z)-isomer. We used the diol 2b after removal of the minor product 2a by using silica gel column chromatography.
23. Ley, S. V.; Norman, J.; Griffith, W. P.; Marsden, S. P. Synthesis 1994, 639.
24. (a) Paquette, L. A.; Crouse, G. D.; Sharma, A. K. J. Am. Chem. Soc. 1980, 102, 3972.
25. (b) Paquette, L. A.; Crouse, G. D. Tetrahedron, Supplement 1981, 37, 281.
26. Johnson, W. S.; Bartlett, W. R.; Czeskis, B. A.; Gautier, A.; Lee, C. H. ; Lemoine, R.; Leopold, E. J.; Luedtke, G. R. Bancroft, K. J., J. Org. Chem. 1999, 64, 9587.
27. 4).
28. 2Si, 224.1233; found, 224.1222.
29. Boeckman, R. K., Jr.; Bruza, K. J. Tetrahedron Lett. 1974, 3365.
30. Dess, D. B.; Martin, J. C. J. Am. Chem. Soc. 1991, 113, 7277.
31. Hubschwerlen, C.; Angehrn, P.; Gubernator, K.; Page, M. G. P.; Specklin, J.-L. J. Med. Chem. 1998, 41, 3972.
32. Smith, J. G.; Drozda, S. E.; Petraglia, S. P.; Quinn, N. R.; Rice, E. M. ; Taylor, B. S.; Viswanathan, M. J. Org. Chem. 1984, 49, 4112.
33. The numbering for a fatty acid was used.
34. All new compounds gave the expected analytical (combustion and/or high-resolution mass) and spectral (IR, NMR, and mass) data.