Synthesis of both the enantiomers of methyl tuberonate, natural methyl β-D-glucopyranosyloxyjasmonate and its epimer

Tetrahedron

Volumn 55, Issue 15, 1999, Pages 4621-4630

  Inoue, Munenori ^a   Kitahara, Takeshi ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BETA DEXTRO GLUCOPYRANOSYLOXYJASMONIC ACID METHYL ESTER; DICHLOROACETIC ACID; JASMONIC ACID; TRIFLUOROACETIC ACID; TUBERONIC ACID METHYL ESTER; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; ENANTIOMER; LYSIS; PLANT GROWTH; PRIORITY JOURNAL; STEREOCHEMISTRY; SYNTHESIS;

EID: 0033537893     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(99)00157-X     Document Type: Article

References (33)

1. Demole, E.; Lederer, E.; Mercier, D. Helv. Chim. Acta 1962, 45, 675., Demole, E.; Stoll, M. Helv. Chim. Acta 1962, 45, 692.
2. Demole, E.; Lederer, E.; Mercier, D. Helv. Chim. Acta 1962, 45, 675., Demole, E.; Stoll, M. Helv. Chim. Acta 1962, 45, 692.
3. Koda, Y.; Omer, E-S. A.; Yoshihara, T.; Shibata, H.; Sakamura, S.; Okazawa, Y. Plant Cell Physiol., 1988, 29, 1047., Yoshihara, T.; Omer, E-S. A.; Koshino, H.; Sakamura, S.; Kikuta, Y.; Koda, Y. Agric. Biol. Chem. 1989, 53, 2835.
4. Koda, Y.; Omer, E-S. A.; Yoshihara, T.; Shibata, H.; Sakamura, S.; Okazawa, Y. Plant Cell Physiol., 1988, 29, 1047., Yoshihara, T.; Omer, E-S. A.; Koshino, H.; Sakamura, S.; Kikuta, Y.; Koda, Y. Agric. Biol. Chem. 1989, 53, 2835.
5. Matsuura, H.; Yoshihara, T.; Ichihara, A.; Kikuta, Y.; Koda, Y. Biosci. Biotech. Biochem. 1993, 57, 1253.
6. Fujita, T.; Terato, K.; Nakayama, M. Biosci. Biotech. Biochem. 1996, 60, 732.
7. Aldridge, D. C.; Galt, S.; Griles, D.; Turner, W. D. J Chem. Soc (D) 1971, 1623., Fukui, H.; Koshimizu, K.; Usuda, S.; Yamazaki, Y. Agric. Biol. Chem. 1977, 41 175., Yamane. H.; Takagi, H.; Abe, H.; Yokota, T.; Takahasi, N. Plant Cell Physiol. 1981, 22, 689. Koda, Y. Physiologia Plantarum 1997, 100, 639. Tamogami, S.; Rakwal, R.; Kodama, O. FEBS Letters 1997, 412, 61. and references cited therein.
8. Aldridge, D. C.; Galt, S.; Griles, D.; Turner, W. D. J Chem. Soc (D) 1971, 1623., Fukui, H.; Koshimizu, K.; Usuda, S.; Yamazaki, Y. Agric. Biol. Chem. 1977, 41 175., Yamane. H.; Takagi, H.; Abe, H.; Yokota, T.; Takahasi, N. Plant Cell Physiol. 1981, 22, 689. Koda, Y. Physiologia Plantarum 1997, 100, 639. Tamogami, S.; Rakwal, R.; Kodama, O. FEBS Letters 1997, 412, 61. and references cited therein.
9. Aldridge, D. C.; Galt, S.; Griles, D.; Turner, W. D. J Chem. Soc (D) 1971, 1623., Fukui, H.; Koshimizu, K.; Usuda, S.; Yamazaki, Y. Agric. Biol. Chem. 1977, 41 175., Yamane. H.; Takagi, H.; Abe, H.; Yokota, T.; Takahasi, N. Plant Cell Physiol. 1981, 22, 689. Koda, Y. Physiologia Plantarum 1997, 100, 639. Tamogami, S.; Rakwal, R.; Kodama, O. FEBS Letters 1997, 412, 61. and references cited therein.
10. Aldridge, D. C.; Galt, S.; Griles, D.; Turner, W. D. J Chem. Soc (D) 1971, 1623., Fukui, H.; Koshimizu, K.; Usuda, S.; Yamazaki, Y. Agric. Biol. Chem. 1977, 41 175., Yamane. H.; Takagi, H.; Abe, H.; Yokota, T.; Takahasi, N. Plant Cell Physiol. 1981, 22, 689. Koda, Y. Physiologia Plantarum 1997, 100, 639. Tamogami, S.; Rakwal, R.; Kodama, O. FEBS Letters 1997, 412, 61. and references cited therein.
11. Aldridge, D. C.; Galt, S.; Griles, D.; Turner, W. D. J Chem. Soc (D) 1971, 1623., Fukui, H.; Koshimizu, K.; Usuda, S.; Yamazaki, Y. Agric. Biol. Chem. 1977, 41 175., Yamane. H.; Takagi, H.; Abe, H.; Yokota, T.; Takahasi, N. Plant Cell Physiol. 1981, 22, 689. Koda, Y. Physiologia Plantarum 1997, 100, 639. Tamogami, S.; Rakwal, R.; Kodama, O. FEBS Letters 1997, 412, 61. and references cited therein.
12. Koda, Y.; Kikuda, Y.; Kitahara, T.; Nishi, T.; Mori, K. Phytochemistry 1992, 31, 1111.
13. Examples of synthesis of racemic methyl jasmonate and/or methyl epijasmonate Büchi, O.; Egger, B. J. Org. Chem. 1971, 36, 2021., Kitahara, T.; Mori, K.; Matsui, M.; Iwamoto, M.; Takagi, Y.; Warita, Y. Agric. Biol. Chem. 1982, 46, 1639., Tanaka, H.; Torii, S. J. Org. Chem. 1975, 40, 462., Kataoka, H.; Yamada, K.; Goto, K.; Tsuji, J. Tetrahedron 1987, 43, 4107., Seto, H.; Yoshioka, H. Chem. Lett. 1990, 51, 1797., Stork, G.; Ouerfelli, O. New. J. Chem. 1992, 16, 95. and referrences cited therein.
14. Examples of synthesis of racemic methyl jasmonate and/or methyl epijasmonate Büchi, O.; Egger, B. J. Org. Chem. 1971, 36, 2021., Kitahara, T.; Mori, K.; Matsui, M.; Iwamoto, M.; Takagi, Y.; Warita, Y. Agric. Biol. Chem. 1982, 46, 1639., Tanaka, H.; Torii, S. J. Org. Chem. 1975, 40, 462., Kataoka, H.; Yamada, K.; Goto, K.; Tsuji, J. Tetrahedron 1987, 43, 4107., Seto, H.; Yoshioka, H. Chem. Lett. 1990, 51, 1797., Stork, G.; Ouerfelli, O. New. J. Chem. 1992, 16, 95. and referrences cited therein.
15. Examples of synthesis of racemic methyl jasmonate and/or methyl epijasmonate Büchi, O.; Egger, B. J. Org. Chem. 1971, 36, 2021., Kitahara, T.; Mori, K.; Matsui, M.; Iwamoto, M.; Takagi, Y.; Warita, Y. Agric. Biol. Chem. 1982, 46, 1639., Tanaka, H.; Torii, S. J. Org. Chem. 1975, 40, 462., Kataoka, H.; Yamada, K.; Goto, K.; Tsuji, J. Tetrahedron 1987, 43, 4107., Seto, H.; Yoshioka, H. Chem. Lett. 1990, 51, 1797., Stork, G.; Ouerfelli, O. New. J. Chem. 1992, 16, 95. and referrences cited therein.
16. Examples of synthesis of racemic methyl jasmonate and/or methyl epijasmonate Büchi, O.; Egger, B. J. Org. Chem. 1971, 36, 2021., Kitahara, T.; Mori, K.; Matsui, M.; Iwamoto, M.; Takagi, Y.; Warita, Y. Agric. Biol. Chem. 1982, 46, 1639., Tanaka, H.; Torii, S. J. Org. Chem. 1975, 40, 462., Kataoka, H.; Yamada, K.; Goto, K.; Tsuji, J. Tetrahedron 1987, 43, 4107., Seto, H.; Yoshioka, H. Chem. Lett. 1990, 51, 1797., Stork, G.; Ouerfelli, O. New. J. Chem. 1992, 16, 95. and referrences cited therein.
17. Examples of synthesis of racemic methyl jasmonate and/or methyl epijasmonate Büchi, O.; Egger, B. J. Org. Chem. 1971, 36, 2021., Kitahara, T.; Mori, K.; Matsui, M.; Iwamoto, M.; Takagi, Y.; Warita, Y. Agric. Biol. Chem. 1982, 46, 1639., Tanaka, H.; Torii, S. J. Org. Chem. 1975, 40, 462., Kataoka, H.; Yamada, K.; Goto, K.; Tsuji, J. Tetrahedron 1987, 43, 4107., Seto, H.; Yoshioka, H. Chem. Lett. 1990, 51, 1797., Stork, G.; Ouerfelli, O. New. J. Chem. 1992, 16, 95. and referrences cited therein.
18. Examples of synthesis of racemic methyl jasmonate and/or methyl epijasmonate Büchi, O.; Egger, B. J. Org. Chem. 1971, 36, 2021., Kitahara, T.; Mori, K.; Matsui, M.; Iwamoto, M.; Takagi, Y.; Warita, Y. Agric. Biol. Chem. 1982, 46, 1639., Tanaka, H.; Torii, S. J. Org. Chem. 1975, 40, 462., Kataoka, H.; Yamada, K.; Goto, K.; Tsuji, J. Tetrahedron 1987, 43, 4107., Seto, H.; Yoshioka, H. Chem. Lett. 1990, 51, 1797., Stork, G.; Ouerfelli, O. New. J. Chem. 1992, 16, 95. and referrences cited therein.
19. Examples of enantioselective synthesis of methyl jasmonate and/or methyl epijasmonate Quinkert, G.; Adam, F.; Durner, G. Angew. Chem. Int. Ed. Engl. 1982, 21, 856., Posner, G. H.; Asirvastham, E.; Ali, S. F. J. Chem. Soc., Chem. Commun. 1985, 852., Weings, K.; Gethoffer, H.; Huber-Patz, U.; Rodewald, H.; Irngartinger, H. Liebigs Ann. Chem. 1987. 361., Helmchen, G.; Goeke, A.; Lauer, O.; Urmann, M.; Fries, J. Angew. Chem. Int. Ed. Engl. 1990, 29, 1024., Crombie, L.; Mistry, K. M. J. Chem. Soc., Perkin Trans. 1 1991, 1981., Taapken, T.; Blechdert, S.; Weilier E. W.; Zenk, M. H. J. Chem. Soc., Perkin Trans. 1 1994, 1439., Roth, G. J; Kirschbaum, S; Bestmann, H. J. Synlett 1997, 618.
20. Examples of enantioselective synthesis of methyl jasmonate and/or methyl epijasmonate Quinkert, G.; Adam, F.; Durner, G. Angew. Chem. Int. Ed. Engl. 1982, 21, 856., Posner, G. H.; Asirvastham, E.; Ali, S. F. J. Chem. Soc., Chem. Commun. 1985, 852., Weings, K.; Gethoffer, H.; Huber-Patz, U.; Rodewald, H.; Irngartinger, H. Liebigs Ann. Chem. 1987. 361., Helmchen, G.; Goeke, A.; Lauer, O.; Urmann, M.; Fries, J. Angew. Chem. Int. Ed. Engl. 1990, 29, 1024., Crombie, L.; Mistry, K. M. J. Chem. Soc., Perkin Trans. 1 1991, 1981., Taapken, T.; Blechdert, S.; Weilier E. W.; Zenk, M. H. J. Chem. Soc., Perkin Trans. 1 1994, 1439., Roth, G. J; Kirschbaum, S; Bestmann, H. J. Synlett 1997, 618.
21. Examples of enantioselective synthesis of methyl jasmonate and/or methyl epijasmonate Quinkert, G.; Adam, F.; Durner, G. Angew. Chem. Int. Ed. Engl. 1982, 21, 856., Posner, G. H.; Asirvastham, E.; Ali, S. F. J. Chem. Soc., Chem. Commun. 1985, 852., Weings, K.; Gethoffer, H.; Huber-Patz, U.; Rodewald, H.; Irngartinger, H. Liebigs Ann. Chem. 1987. 361., Helmchen, G.; Goeke, A.; Lauer, O.; Urmann, M.; Fries, J. Angew. Chem. Int. Ed. Engl. 1990, 29, 1024., Crombie, L.; Mistry, K. M. J. Chem. Soc., Perkin Trans. 1 1991, 1981., Taapken, T.; Blechdert, S.; Weilier E. W.; Zenk, M. H. J. Chem. Soc., Perkin Trans. 1 1994, 1439., Roth, G. J; Kirschbaum, S; Bestmann, H. J. Synlett 1997, 618.
22. Examples of enantioselective synthesis of methyl jasmonate and/or methyl epijasmonate Quinkert, G.; Adam, F.; Durner, G. Angew. Chem. Int. Ed. Engl. 1982, 21, 856., Posner, G. H.; Asirvastham, E.; Ali, S. F. J. Chem. Soc., Chem. Commun. 1985, 852., Weings, K.; Gethoffer, H.; Huber-Patz, U.; Rodewald, H.; Irngartinger, H. Liebigs Ann. Chem. 1987. 361., Helmchen, G.; Goeke, A.; Lauer, O.; Urmann, M.; Fries, J. Angew. Chem. Int. Ed. Engl. 1990, 29, 1024., Crombie, L.; Mistry, K. M. J. Chem. Soc., Perkin Trans. 1 1991, 1981., Taapken, T.; Blechdert, S.; Weilier E. W.; Zenk, M. H. J. Chem. Soc., Perkin Trans. 1 1994, 1439., Roth, G. J; Kirschbaum, S; Bestmann, H. J. Synlett 1997, 618.
23. Examples of enantioselective synthesis of methyl jasmonate and/or methyl epijasmonate Quinkert, G.; Adam, F.; Durner, G. Angew. Chem. Int. Ed. Engl. 1982, 21, 856., Posner, G. H.; Asirvastham, E.; Ali, S. F. J. Chem. Soc., Chem. Commun. 1985, 852., Weings, K.; Gethoffer, H.; Huber-Patz, U.; Rodewald, H.; Irngartinger, H. Liebigs Ann. Chem. 1987. 361., Helmchen, G.; Goeke, A.; Lauer, O.; Urmann, M.; Fries, J. Angew. Chem. Int. Ed. Engl. 1990, 29, 1024., Crombie, L.; Mistry, K. M. J. Chem. Soc., Perkin Trans. 1 1991, 1981., Taapken, T.; Blechdert, S.; Weilier E. W.; Zenk, M. H. J. Chem. Soc., Perkin Trans. 1 1994, 1439., Roth, G. J; Kirschbaum, S; Bestmann, H. J. Synlett 1997, 618.
24. Examples of enantioselective synthesis of methyl jasmonate and/or methyl epijasmonate Quinkert, G.; Adam, F.; Durner, G. Angew. Chem. Int. Ed. Engl. 1982, 21, 856., Posner, G. H.; Asirvastham, E.; Ali, S. F. J. Chem. Soc., Chem. Commun. 1985, 852., Weings, K.; Gethoffer, H.; Huber-Patz, U.; Rodewald, H.; Irngartinger, H. Liebigs Ann. Chem. 1987. 361., Helmchen, G.; Goeke, A.; Lauer, O.; Urmann, M.; Fries, J. Angew. Chem. Int. Ed. Engl. 1990, 29, 1024., Crombie, L.; Mistry, K. M. J. Chem. Soc., Perkin Trans. 1 1991, 1981., Taapken, T.; Blechdert, S.; Weilier E. W.; Zenk, M. H. J. Chem. Soc., Perkin Trans. 1 1994, 1439., Roth, G. J; Kirschbaum, S; Bestmann, H. J. Synlett 1997, 618.
25. Examples of enantioselective synthesis of methyl jasmonate and/or methyl epijasmonate Quinkert, G.; Adam, F.; Durner, G. Angew. Chem. Int. Ed. Engl. 1982, 21, 856., Posner, G. H.; Asirvastham, E.; Ali, S. F. J. Chem. Soc., Chem. Commun. 1985, 852., Weings, K.; Gethoffer, H.; Huber-Patz, U.; Rodewald, H.; Irngartinger, H. Liebigs Ann. Chem. 1987. 361., Helmchen, G.; Goeke, A.; Lauer, O.; Urmann, M.; Fries, J. Angew. Chem. Int. Ed. Engl. 1990, 29, 1024., Crombie, L.; Mistry, K. M. J. Chem. Soc., Perkin Trans. 1 1991, 1981., Taapken, T.; Blechdert, S.; Weilier E. W.; Zenk, M. H. J. Chem. Soc., Perkin Trans. 1 1994, 1439., Roth, G. J; Kirschbaum, S; Bestmann, H. J. Synlett 1997, 618.
26. Kitahara, T.; Nishi, T.; Mori, K. Tetrahedron 1991, 47, 6999.
27. Kitahara, T.; Inoue, M.; Tamogami, S.; Kaiser, R. Tetrahedron 1996, 52, 1487.
28. Nishi, T.; Kitahara, T. Proc. Japan Acad. Ser. B 1995, 71, 20.
29. Schow, R. S.; McMorris, T. C. J. Org. Chem 1979, 44, 3760.
30. 10 No trans-isomer was detected.
31. Ogawa, Y.; Shibasaki, M. Tetrahedron Letters 1984, 25, 663.
32. Dess, D. B.; Martin, J.C. J. Am. Chem. Soc. 1991, 113, 7227.
33. Martos, M. B.; Korosy, F. Nature 1950, 165, 369,