A divergent synthesis of triyne natural products and glycosylated analogues using a carbenoid rearrangement

Synthesis

Volumn , Issue 18, 2005, Pages 3167-3178

  Luu, Thanh ^a   Shi, Wei ^a   Lowary, Todd L ^a   Tykwinski, Rik R ^a  

^a UNIVERSITY OF ALBERTA   (Canada)

Author keywords

Carbenoids; Carbohydrates; Fritsch Buttenberg Wiechell reaction; Natural products; Polyacetylenes; Polyynes

Indexed keywords

CARBOHYDRATES; POLYACETYLENES; REACTION KINETICS; SYNTHESIS (CHEMICAL);

CARBENOIDS; FRITSC-BUTTENBERG REACTION; POLYYNES;

AMINES;

1,4 BUTYNEDIOL; ACETYLENE DERIVATIVE; ALCOHOL DERIVATIVE; CARBENOID; NATURAL PRODUCT; POLYACETYLENE DERIVATIVE; POLYYNE DERIVATIVE; TRIYNE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CADIOT CHODKIEWICZ REACTION; CONJUGATION; INTERMETHOD COMPARISON; PROTEIN GLYCOSYLATION; REACTION ANALYSIS; REACTION OPTIMIZATION; SONOGASHIRA REACTION; SYNTHESIS;

EID: 28344434554     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2005-918428     Document Type: Article

References (59)

1. The term polyyne is meant to denote compounds with a structural sequence of two or more consecutive (conjugated) acetylene units. The term polyacetylene has been often used in this context as well, but this term can be ambiguous due to its more common use in reference to polymerized acetylene.
2. Plant and fungal sources: (a) Chemistry and Biology of Naturally Occurring Acetylenes and Related Compounds (NOARC); Lam, J.; Breteler, H.; Arnason, T.; Hansen, L., Eds.; Elsevier: New York, 1988.
3. (b) Bohlmann, F.; Burkhardt, H.; Zdero, C. Naturally Occurring Acetylenes; Academic Press: New York, 1973.
4. (c) Christensen, L. P. Phytochemistry 1992, 31, 7.
5. (d) Bohlmann, F. In Chemistry of Acetylenes, Chap. 14; Viehe, H. G., Ed.; Marcel Dekker: New York, 1969, 977-986.
6. (e) Jones, E. R. H.; Thaller, V. In The Chemistry of the Carbon-Carbon Triple Bond, Part 2; Patai, S., Ed.; John Wiley & Sons: New York, 1978, Chap. 14, 621-633.
7. (f) Jones, E. R. H.; Thaller, V. 49n Handbook of Microbiology Microbial Products, Vol. 3; Laskin, A. I.; Lechevalier, H. A., Eds.; CRC Press: Cleveland, 1973, 63-74.
8. (g) Jones, E. R. H. Proc. Chem. Soc., London 1960, 199.
9. From marine sources: (a) Blunt, J. W.; Copp, B. R.; Munro, M. H. G.; Northcote, P. T.; Prinsep, M. R. Nat. Prod. Rep. 2003, 20, 1.
10. (b) Faulkner, D. J. Nat. Prod. Rep. 2002, 19, 1.
11. (c) Faulkner, D. J. Nat. Prod. Rep. 2001, 18, 1.
12. (d) Faulkner, D. J. Nat. Prod. Rep. 2000, 17, 7.
13. From the soldier beetle: Meinwald, J.; Meinwald, Y. C.; Chalmers, A. M.; Eisner, T. Science (Washington, D.C.) 1968, 160, 890; it should be noted, however, that this compound likely derives from the plants which compose the diet of the beetle, see reference 2e.
14. Arnason, J. T.; Philogene, B. J. R.; Berg, C.; MacEachern, A.; Kaminski, J.; Leitch, L. C.; Morand, P.; Lam, J. Phytochemistry 1986, 25, 1609.
15. For example (a) Kobaisy, M.; Abramowski, Z.; Lermer, L.; Saxena, G.; Hancock, R. E. W.; Towers, G. H. N.; Doxsee, D.; Stokes, R. W. J. Nat. Prod. 1997, 60, 1210.
16. (b) Fusetani, N.; Toyoda, T.; Asai, N.; Matsunaga, S.; Maruyama, T. J. Nat. Prod. 1996, 59, 796.
17. Rashid, M. A.; Gustafson, K. R.; Cardellina, J. H. II; Boyd, M. R. Nat. Prod. Lett. 2001, 15, 21.
18. (a) Nakamura, Y.; Kawamoto, N.; Ohio, Y.; Torikai, K.; Murakami, A.; Ohigashi, H. Cancer Lett. 1999, 140, 37.
19. (b) Ito, A.; Cui, B. L.; Chavez, D.; Chai, H. B.; Shin, Y. G.; Kawanishi, K.; Kardono, L. B. S.; Riswan, S.; Farnsworth, N. R.; Cordell, G. A.; Pezzuto, J. M.; Kinghorn, A. D. J. Nat. Prod. 2001, 64, 246.
20. (c) Ahn, B.-Z.; Kim, S.-I. Arch. Pharm. (Weinheim, Ger.) 1988, 321, 61.
21. For leading reviews, see: (a) Gardner, J. N.; Jones, E. R. H.; Leeming, P. R.; Stephenson, J. S. J. Chem. Soc. 1960, 691.
22. (b) Sörensen, N. A. Proc. Chem. Soc., London 1961, 98.
23. (c) Bohlmann, F.; Bornowski, H.; Arndt, C. Fortschr. Chem. Forsch. 1962, 4, 138.
24. (d) Bu'Lock, J. D. Prog. Org. Chem. 1964, 6, 86.
25. For a review of recent polyyne syntheses, see: Shi Shun, A. L. K.; Tykwinski, R. R. Angew. Chem. Int. Ed., in press.
26. For an excellent review of these methods, see: Siemsen, P.; Livingston, R. C.; Diederich, F. Angew. Chem. Int. Ed. 2000, 39, 2633.
27. For reviews, see: (a) Stang, P. J. Chem. Rev. 1978, 78, 383.
28. (b) Knorr, R. Chem. Rev. 2004, 104, 3795.
29. (a) Eisler, S.; Chahal, N.; McDonald, R.; Tykwinski, R. R. Chem. Eur. J. 2003, 9, 2452.
30. (b) Shi Shun, A. L. K.; Chernick, E. T.; Eisler, S.; Tykwinski, R. R. J. Org. Chem. 2003, 68, 1339.
31. (c) Shi Shun, A. L. K.; Tykwinski, R. R. J. Org. Chem. 2003, 68, 6810.
32. For an excellent summary of natural and synthetic acetylenosaccharides, see: Vasella, A. In Acetylene Chemistry - Chemistry, Biology, and Materials Science; Diederich, F.; Stang, P. J.; Tykwinski, R. R., Eds.; Wiley-VCH: Weinheim, 2005, Chap. 5.
33. (a) Livingston, R. C.; Cox, L. R.; Gramlich, V.; Diederich, F. Angew. Chem. Int. Ed. 2001, 40, 2334.
34. (b) Livingston, R.; Cox, L. R.; Odermatt, S.; Diederich, F. Helv. Chim. Acta 2002, 85, 3052.
35. (a) Ramirez, F.; Desai, N. B.; McKelvie, N. J. Am. Chem. Soc. 1962, 84, 1745.
36. (b) Corey, E. J.; Fuchs, P. L. Tetrahedron Lett. 1972, 3769.
37. (c) Posner, G. H.; Loomis, G. L.; Sawaya, H. S. Tetrahedron Lett. 1975, 1373.
38. Mattes, H.; Benezra, C. Tetrahedron Lett. 1987, 28, 1697.
39. McIntosh, M. C.; Weinreb, S. M. J. Org. Chem. 1993, 58, 4823.
40. Anthony, J.; Boldi, A. M.; Rubin, Y.; Hobi, M.; Gramlich, V.; Knobler, C. B.; Seiler, P.; Diederich, F. Helv. Chim. Acta 1995, 78, 13.
41. Hearn, M. T. W.; Jones, E. R. H.; Pellatt, M. G.; Thaller, V.; Turner, J. L. J. Chem. Soc., Perkin Trans, 1 1973, 2785.
42. Compound 21 has been synthesized using the Cadiot-Chodkiewicz protocol, see: (a) Curtis, R. F.; Taylor, J. A. J. Chem. Soc. C 1971, 186.
43. (b) Chodkiewicz, W. Ann. Chim. (Paris) 1957, 2, 819.
44. Bohlmann, F.; Bornowski, H.; Kleine, K.-M. Chem. Ber. 1964, 97, 2135.
45. Bohlmann, F.; Arndt, C.; Kleine, K.-M.; Wotschokowsky, M. Chem. Ber. 1965, 98, 1228.
46. Bendixen, O.; Lam, J.; Kaufmann, F. Phytochemistry 1969, 8, 1021.
47. Compound 26 has been synthesized previously using the Cadiot-Chodkiewicz protocol, see: Prévost, S.; Meier, J.; Chodkiewicz, W.; Cadiot, P.; Willemart, A. Bull. Soc. Chim. Fr. 1961, 2171; compounds 26 and 27 have also been synthesized by Bohlmann, see reference 22.
48. Arnason, T.; Swain, T.; Wat, C.-K.; Graham, E. A.; Parington, S.; Towers, G. H. N.; Lam, J. Biochem. Syst. Ecol. 1981, 9, 63.
49. Wang, N. L.; Yao, X. S.; Ishii, R.; Kitanaka, S. Chem. Pharm. Bull. 2001, 49, 938.
50. Rucker, G.; Kehrbaum, S.; Sakulas, H.; Lawong, B.; Goeltenboth, F. Planta Med. 1992, 58, 266.
51. Ubillas, R. P.; Mendez, C. D.; Jolad, S. D.; Luo, J.; King, S. R.; Carlson, T. J.; Fort, D. M. Planta Med. 2000, 66, 82.
52. New polyacetylene glycosides from Bidens plants as allergy inhibitors. Nissan Chemical Industries, Ltd., Japan: Kitanaka, S.; Yang, H. S.; Wang, H. L.; Ishii, R. Japanese Patent JP 2000-48564, 2000.
53. Gung, B. W.; Fox, R. M. Tetrahedron 2004, 60, 9405.
54. Hanessian, S.; Banoub, J. Methods Carbohydr. Chem. 1980, 8, 243.
55. (a) Bérces, A.; Whitfield, D. M.; Nukuda, T.; do Santos, Z. I.; Obuchowska, A.; Krepinsky, J. J. Can. J. Chem. 2004, 82, 1157.
56. (b) Nukuda, T.; Bérces, A.; Whitfield, D. M. J. Org. Chem. 1999, 64, 9030.
57. (c) Ziegler, T.; Kovac, P.; Glaudemans, C. P. J. Liebigs Ann. Chem. 1990, 613; and references therein.
58. Garegg, P. J.; Norberg, T. Acta Chem. Scand., Ser. B 1979, 33, 116.
59. Schmidt, R. R.; Kinzy, W. Adv. Carbohydr. Chem. Biochem. 1994, 50, 21.