Asymmetric total syntheses of (+)-coronafacic acid and (+)-coronatine, phytotoxins isolated from Pseudomonas Syringae pathovars

Tetrahedron

Volumn 53, Issue 28, 1997, Pages 9509-9524

  Nara, Shinji ^a   Toshima, Hiroaki ^a   Ichihara, Akitami ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CORONAFACIC ACID; CORONATINE; CYCLOPENTENONE DERIVATIVE; ESTER; PLANT TOXIN; UNCLASSIFIED DRUG;

ARTICLE; NONHUMAN; NUCLEAR MAGNETIC RESONANCE; OPTICAL ROTATION; PRIORITY JOURNAL; PSEUDOMONAS SYRINGAE; SYNTHESIS;

PSEUDOMONAS; PSEUDOMONAS SYRINGAE;

EID: 0030745620     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)00614-5     Document Type: Article

References (46)

1. (a) Ichihara, A.; Shiraishi, K.; Sato, H.; Sakamura, S.; Nishiyama, K.; Sakai, R.; Furusaki, A.; Matsumoto, T. J. Am. Chem. Soc. 1977, 99, 636-637.
2. (b) Ichihara, A.; Shiraishi, K.; Sakamura, S.; Nishiyama, K.; Sakai, R. Tetrahedron Lett. 1977, 269-272.
3. (c) Ichihara, A.; Shiraishi, K.; Sakamura, S.; Furusaki, A.; Hashiba, N.; Matsumoto, T. Tetrahedron Lett. 1979, 365-368.
4. A very small amount of 3, as a free amino acid and the biosynthetic intermediate of 1, has been recently isolated from Pseudomonas syringae pv. glycinea. Mitchell, R. E.; Young, S. A.; Bender, C. L. Phytochemistry 1994, 35, 343-348.
5. (a) Mitchell, R. E. Experientia 1991, 47, 791-803.
6. (b) Tamura, K.; Takikawa, Y.; Tsuyumu, S.; Goto, M.; Watanabe, M. Ann. Phytopath. Soc. Japan 1992, 58, 276-281. and references cited therein.
7. (a) Sembdner, G.; Parthier, B. Annu. Rev. Plant Physiol. Plant Mol. Biol. 1993, 44, 596-589.
8. (b) Greulich, F.; Yoshihara, T.; Toshima, H.; Ichihara, A. XV Int. Bot. Congress, Yokohama, 1993. Abstr. 4154, p. 388.
9. (c) Weiler, E. W.; Kutchan, T. M.; Gorba, T.; Brodschelm, W.; Niesel, U.; Bublitz, F. FEBS Lett. 1994, 345, 9-13.
10. (d) Feys, B. J. F.; Benedetti, C. E.; Penfold, C. N.; Turner, J. G. J. Plant Cell 1994, 6, 751-759.
11. (e) Boland, W.; Hopke, J.; Donath, J.; Nuske, J.; Bublitz. F. Angew. Chem. Int. Ed. Engl. 1995, 34, 1600-1601.
12. (f) Krumm, T.; Bandemer, K.; Boland, W. FEBS Lett. 1995, 377, 523-529.
13. (g) Blechert, S.; Brodschelm, W.; Holder, S.; Kammerer, L.; Kutchan, T. M.; Mueller, M. J.; Xia, Z.-Q.; Zenk, M. H. Proc. Natl. Acad. Sci. USA 1995, 92, 4099-4105.
14. (h) Greulich, F.; Yoshihara, T.; Ichihara, A. J. Plant Physiol. 1996, 147, 359-366.
15. (i) Krumm, T.; Boland, W. Molecules 1996, 1, 23-26.
16. (j) Koda, Y.; Takahashi, K.; Kikuta, Y.; Greulich, F.; Toshima, H.; Ichihara, A. Phytochemistry 1996, 41, 93-96.
17. (a) Ichihara, A.; Kimura, R.; Moriyasu, K.; Sakamura, S. Tetrahedron Lett. 1977, 4331-4334.
18. (b) Ichihara, A.; Kimura, R.; Yamada, S.; Sakamura, S. J. Am. Chem. Soc. 1980, 102, 6353-6355.
19. (c) Jung, M. E.; Hudspeth, J. P. J. Am. Chem. Soc. 1980, 102, 2463-2464.
20. (d) Tsuji, J. Pure Appl. Chem. 1981, 53, 2371-2378.
21. (e) Nakayama, M.; Ohira, S.; Okamura, Y.; Soga, S. Chem. Lett. 1981, 731-732.
22. (f) Jung M. E.; Halweg, K. M. Tetrahedron Lett. 1981, 22, 2735-2738.
23. (g) Nakayama, M.; Ohira, S. Agric. Biol. Chem. 1983, 47, 1689-1690.
24. (h) Liu, H.-J.; Llinas-Brunet, M. Can. J. Chem. 1984, 62, 1747-1750.
25. (i) Ohira, S. Bull. Chem. Soc. Jpn. 1984, 57, 1902-1907.
26. (j) Bhamare, N. K.; Granger, T.; Macas, T. S.; Yates, P. J. Chem. Soc., Chem. Commun. 1990, 739-740.
27. (k) Yates, P.; Bhamare, N. K.; Granger, T.; Macas, T. S. Can. J. Chem. 1993, 71, 995-1001.
28. (l) Mehta, G.; Praveen, M. J. Chem. Soc., Chem. Commun. 1993, 1573-1575.
29. (m) Hölder, S.; Blechert, S. Synlett. 1996, 505.
30. The preliminary results have been partly communicated: (a) Nara, S.; Toshima, H.; Ichihara, A. Tetrahedron Lett. 1996, 37, 6745-6748.
31. (b) Toshima, H.; Nara, S.; Ichihara, A. Biosci. Biotech. Biochem., 1997, 61, 752-753.
32. Toshima, H.; Ichihara, A. Biosci. Biotech. Biochem., 1995, 59, 495-500.
33. McMurry, J. E.; Andrus, W. A.; Musser, J. H. Synthetic Commun. 1978, 8, 53-57.
34. The NOE-enhancement as shown below was observed. This result is explicable that 11 possesses (E)-geometry and s-cis conformation. (formula presented)
35. The (E)-geometry of lithium enolate of 7 was determined as the corresponding silyl enol ether 7a (LDA/ THF, then TMSC1). The NOE-enhancement of the olefinic proton was observed by the irradiation of the methyl protons in the TMS group. In two possible 6-membered chair-like transition states (T1 and T2), T1 predominates over T2 because the steric hindrance between the bulky cyclopentane moiety of the enolate and the alkenyl moiety of the aldehyde contributes unfavorably in T2. In T1, the interaction between the cyclopentane moiety and the hydrogen is not significant in contrast to T2. Therefore, aldol condensation proceeds exclusively via T1 to give syn-products (11a and 10b). (formula presented)
36. (a) Deardorff, D. R.; Matthews, A. J.; McMeekin, D. S.; Craney, C. L. Tetrahedron Lett. 1986, 27, 1255-1256.
37. (b) Myers, A. G.; Hammond, M.; Wu, Y. Tetrahedron Lett. 1996, 37, 3083-3086, and many references cited therein.
38. Grebe, H.; Lange, A.; Riechers, H.; Kieslich, K.; Viergutz, W.; Washausen, P.; Winterfelt, E. J. Chem. Soc., Perkin Trans. 1 1991, 2651-2655.
39. Column: CHIRALCEL OC® (φ4.6 × 250 mm), Eluent: hexane/2-propanol (96/4), Flow rate: 0.3 ml/min. Detection: UV 220 nm, Retention time: (+)-7/ 36 min; (-)-7/ 40 min
40. (a) Sasai, H.; Arai, T.; Shibasaki, M. J. Am. Chem. Soc. 1994, 116, 1571-1572.
41. (b) Arai, T.; Sasai, H.; Aoe, K.; Okamura, K.; Date, T.; Shibasaki, M. Angew. Chem. Int. Ed. Engl. 1996, 35, 104-106.
42. (c) Arai, T.; Yamada, Y. M. A.; Yamamoto, N.; Sasai, H.; Shibasaki, M. Chem. Eur. J. 1996, 2, 1386-1372.
43. Column: CHIRALCEL OC® (φ4.6 × 250 mm), Eluent: hexane/2-propanol (96/4), Flow rate: 0.3 ml/min, Detection: UV 240 nm, Retention time: (+)-5a/ 64 min; (-)-5a/ 59 min
44. The acidic hydrolysis of 5a is heterogeneous reaction and requires vigourous stirring under refluxing conditions. Therefore, the effectiveness of stirring influences the reaction period and yields. The smaller scale-reactions (well-stirred conditions) provide high yields within shorter time in our experience. In contrast to this, the larger scale-reactions provide moderate yields caused by the appearence of decomposed tarry matter, depending on elongation of reaction time. The conditions using co-solvent have been examining.
45. 20 +109°) and our natural sample in ref. 3g.
46. 20+78.8° (c 1.20, MeOH).