Synthesis of naturally occurring acetylenes via an alkylidene carbenoid rearrangement

Journal of Organic Chemistry

Volumn 68, Issue 17, 2003, Pages 6810-6813

  Shi Shun, Annabelle L K ^a   Tykwinski, Rik R ^a  

^a UNIVERSITY OF ALBERTA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

PRECURSORS;

ALDEHYDES; CARBOXYLIC ACIDS; OLEFINS; SYNTHESIS (CHEMICAL);

ACETYLENE;

ACETYLENE DERIVATIVE; ALDEHYDE; CARBENOID; CARBOXYLIC ACID; HALOGEN; LARVICIDAL AGENT; LITHIUM;

ACETYLATION; ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; ION EXCHANGE; SYNTHESIS; TOXICITY TESTING;

ACETYLENE; ALKENES; ALKYLATION; INDICATORS AND REAGENTS; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR;

EID: 0043009833     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo034734g     Document Type: Article

References (51)

1. (a) Busvine, J. R. Disease Transmission by Insects - Its Discovery and 90 Years of Effort to Prevent It; Springer-Verlag: Berlin, Germany, 1993.
2. (b) Baqar, S.; Hayes, C. G.; Murphy, J. R.; Watts, D. M. Am. J. Trop. Med. Hyg. 1993, 48, 757-762.
3. (a) Towers, G. H. N.; Wat, C. K.; Lambert, J. D. H.; Arnason, J. T. Canadian Patent 1173743, 1984.
4. (b) Biologically Active Natural Products - Potential Use in Agriculture; Cutler, H. G., Ed.; ACS Symp. Ser. No. 380; American Chemical Society: Washington, DC, 1988.
5. (a) Jones, E. R. H. Proc. Chem. Soc., London 1960, 199-210.
6. (b) Sörensen, N. A. Proc. Chem. Soc., London 1961, 98-110.
7. (c) Bohlmann, F.; Bornowski, H.; Arndt, C. Fortsch. Chem. Forsch. 1962, 4, 138-272.
8. (d) Bu'Lock, J. D. Prog. Org. Chem. 1964, 6, 86-134.
9. (e) Bohlmann, F. Fortsch. Chem. Forsch. 1966, 6, 65-100.
10. (f) Bohlmann, F. In Chemistry of Acetylenes; Viehe, H. G., Ed.; Marcel Dekker: New York, 1969; Chapter 14, pp 977-986.
11. Gardner, J. N.; Jones, E. R. H.; Leeming, P. R.; Stephenson, J. S. J. Chem. Soc. 1960, 691-697.
12. (a) Dai, J.-R.; Hallock, Y. F.; Cardellina, J. H., II; Gray, G. N.; Boyd, M. R. J. Nat. Prod. 1996, 59, 860-865.
13. (b) Faulkner, D. J. Nat. Prod. Rep. 2000, 17, 7-55.
14. (c) Faulkner, D. J. Nat. Prod. Rep. 2002, 19, 1-48.
15. (d) Nakao, Y.; Uehara, T.; Matunaga, S.; Fusetani, N.; van Soest, R. W. M. J. Nat. Prod. 2002, 65, 922-924.
16. Chemistry and Biology of Naturally-Occurring Acetylenes and Related Compounds (NOARC); Lam, J., Breteler, H., Arnason, T., Hansen, L., Eds.; Bioactive Molecules, Vol. 7; Elsevier: New York, 1988.
17. (a) Arnason, J. T.; Philogène, B. J. R.; Berg, C.; MacEachern, A. ; Kaminski, J.; Leitch, L. C.; Morand, P.; Lam, J. Phytochemistry 1986, 25, 1609-1611.
18. (b) Wat, C.-K.; Prasad, S. K.; Graham, E. A.; Partington, S.; Arnason, T.; Towers, G. H. N.; Lam, J. Biochem. Syst. Ecol. 1981, 9, 59-62.
19. (c) Arnason, T.; Swain, T.; Wat, C.-K.; Graham, E. A.; Partington, S.; Towers, G. H. N. Biochem. Syst. Ecol. 1981, 9, 63-68.
20. (a) Bohlmann, F.; von Kap-Herr, W.; Fanghänel, L.; Arndt, C. Chem. Ber. 1965, 98, 1411-1415.
21. (b) Bohlmann, F.; Burkhardt, H.; Zdero, C. Naturally Occurring Acetylenes; Academic Press: New York, 1973.
22. (c) Bohlmann, F.; Fanghänel, L.; Kleine, K.-M.; Kramer, H.-D.; Mönch, H.; Schuber, J. Chem. Ber. 1965, 98, 2596-2604.
23. (a) Wat, C.-K.; Biswas, R. K.; Graham, E. A.; Bohm, L.; Towers, G. H. N. ; Waygood, E. R. J. Nat. Prod. 1979, 42, 103-111.
24. (b) Alvarez, L.; Marquina, S.; Villarreal, M. L.; Alonso, D.; Aranda, E. ; Delgado, G. Planta Med. 1996, 62, 355-357.
25. (a) Nakajima, S.; Kawazu, K. Agric. Biol. Chem. 1980, 44, 1529-1533.
26. (b) Kawazu, K.; Nishii , Y.; Nakajima, S. Agric. Biol. Chem. 1980, 44, 903-906.
27. (a) Yosioka, I.; Hikino, H.; Sasaki, Y. Chem. Pharm. Bull. 1960, 8, 949-951.
28. (b) Yosioka, I.; Hikino, H.; Sasaki, Y. Chem. Pharm. Bull. 1960, 8, 952-956.
29. (c) Wat, C.-K.; Johns, T.; Towers, G. H. N. J. Ethnopharm. 1980, 2, 279-290.
30. (d) Ding, H.-Y.; Wu, Y.-C.; Lin, H.-C. J. Chin. Chem. Soc. (Taipei) 2000, 47, 561-566.
31. (e) Resch, M.; Heilmann, J.; Steigel, A.; Bauer, R. Planta Med. 2001, 67, 437-442.
32. The ene-triyne 1 has previously been synthesized by Bohlmann et al. using a Wittig reaction, ref 8a.
33. 1-Phenylhepta-1,3,5-triyne (2) has previously been synthesized by Cadiot-Chodkiewicz coupling and elimination protocols: (a) Meier, J.; Chodkiewicz, W.; Cadiot, P.; Willemart, A. C. R. Hebd. Séances Acad. Sci. 1957, 245, 1634-1636. (b) Mavrov, M. V.; Kucherov, V. F. Bull. Acad. Sci. USSR Div. Chem. Sci. (Engl. Transl.) 1966, 833-836. (c) Shim, S. C.; Lee, T. S. Bull. Korean Chem. Soc. 1986, 7, 357-362.
34. 1-Phenylhepta-1,3,5-triyne (2) has previously been synthesized by Cadiot-Chodkiewicz coupling and elimination protocols: (a) Meier, J.; Chodkiewicz, W.; Cadiot, P.; Willemart, A. C. R. Hebd. Séances Acad. Sci. 1957, 245, 1634-1636. (b) Mavrov, M. V.; Kucherov, V. F. Bull. Acad. Sci. USSR Div. Chem. Sci. (Engl. Transl.) 1966, 833-836. (c) Shim, S. C.; Lee, T. S. Bull. Korean Chem. Soc. 1986, 7, 357-362.
35. 1-Phenylhepta-1,3,5-triyne (2) has previously been synthesized by Cadiot-Chodkiewicz coupling and elimination protocols: (a) Meier, J.; Chodkiewicz, W.; Cadiot, P.; Willemart, A. C. R. Hebd. Séances Acad. Sci. 1957, 245, 1634-1636. (b) Mavrov, M. V.; Kucherov, V. F. Bull. Acad. Sci. USSR Div. Chem. Sci. (Engl. Transl.) 1966, 833-836. (c) Shim, S. C.; Lee, T. S. Bull. Korean Chem. Soc. 1986, 7, 357-362.
36. Atractylodin (3) has been synthesized by oxidative coupling, but no yield was reported: Yosioka, I.; Hikino, H.; Sasaki, Y. Chem. Pharm. Bull. 1960, 8, 957-959.
37. (a) Fritsch, P. Liebigs Ann. Chem. 1894, 279, 319-323.
38. (b) Buttenberg, W. P. Liebigs Ann. Chem. 1894, 279, 324-337.
39. (c) Wiechell, H. Liebigs Ann. Chem. 1894, 279, 337-344.
40. (a) Eisler, S.; Tykwinski, R. R. J. Am. Chem. Soc. 2000, 122, 10736-10737.
41. (b) Chernick, E. T.; Eisler, S.; Tykwinski, R. R. Tetrahedron Lett. 2001, 42, 8575-8578.
42. (c) Shi Shun, A. L. K.; Chernick, E. T.; Eisler, S.; Tykwinski, R. R. J. Org. Chem. 2003, 68, 1339-1347.
43. (d) Eisler, S.; Chahal, N.; McDonald, R.; Tykwinski, R. R. Chem. Eur. J. 2003, 9, 2542-2550.
44. Transformation of the terminal triyne into its methylated derivative 1 required that THF be used as solvent. Use of diethyl ether was unsuccessful, consistent with that observed by Holmes and Jones in a similar methylation reaction, see: Holmes, A. B.; Jones, E. G. Tetrahedron Lett. 1980, 21, 3111-3112.
45. Solladié, G.; Colobert, F.; Kalaï, C. Tetrahedron Lett. 2000, 41, 4197-4200.
46. Rule, G. N.; Detty, M. R.; Kaeding, J. E.; Sinicropi, J. A. J. Org. Chem. 1995, 60, 1665-1673.
47. Bestmann, H. J.; Frey, H. Liebigs Ann. Chem. 1980, 2061-2071.
48. Empirical evidence suggests that lithium-halogen exchange is more rapid than quenching of the n-BuLi by adventitious water. Any water present in the reaction medium therefore results in in situ protonation of the carbenoid intermediate. This extensively complicates purification because of similar retention times on common chromatographic supports, thus reiterating the need for strictly anhydrous reagents and reaction conditions.
49. (a) Shim, S. C.; Lee, T. S. Chem. Lett. 1986, 1075-1078.
50. (b) Chang, M. H.; Wang, G. J.; Kuo, Y. H.; Lee, C. K. J. Chin. Chem. Soc. 2000, 47, 1131-1136.
51. Nishikawa, Y.; Yasuda, I.; Watanabe, Y.; Seto, T. Yakugaku Zasshi 1976, 96, 1322-1326.