Iterative, Stereoselective Homologation of Chiral Polyalkoxy Aldehydes Employing 2-(Trimethylsilyl)thiazole as a Formyl Anion Equivalent. The Thiazole Route to Higher Carbohydrates

Journal of Organic Chemistry

Volumn 54, Issue 3, 1989, Pages 693-702

  Dondoni, Alessandro ^a   Fantin, Giancarlo ^a   Fogagnolo, Marco ^a   Medici, Alessandro ^a   Pedrini, Paola ^a  

^a UNIVERSITY OF FERRARA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000772702     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00264a035     Document Type: Article

References (35)

1. This is the lecture presented by the senior author (A. D.) at the 5th European Symposium on Organic Chemistry (Jerusalem, Israel, August, 1987). For previous partial reports, see: (a) Dondoni, A.; Fo-Gagnolo, M.; Medici, A.; Pedrini, P. Tetrahedron Lett. 1985, 26, 5477. Dondoni, A. Lect. Heterocycl. Chem. 1985, 8, 13, (c) Dondoni, A.; Fantin, G.; Fogagnolo, M.; Medici, A. Angew. Chem., Int. Ed. Engl. 1986, 25, 835. (d) Dondoni, A.; Fantin, G.; Fogagnolo, M.; Medici, A. Tetrahedron 1987, 43, 3533. (e) Dondoni, A.; Fantin, G.; Fogagnolo, M.; Medici, A. J. Chem. Soc., Chem. Commun. 1988, 10.
2. Although the term “synthon” is currently employed to indicate a useful reagent in organic synthesis, we prefer to keep the original definition that is “an idealized chemical species or fragment resulting from a disconnection”: Corey, E. J. Pure Appl. Chem. 1967, 14, 191. See also: Warren, S. Organic Synthesis: The Disconnection Approach; Wiley: New York, 1982. Fuhrhop, J.; Penzlin, G. Organic Synthesis; Verlag Chemie: Weinheim. 1984.
3. Candy, D. Biological Function of Carbohydrates; Wiley: New York, 1980. Kennedy, J. F.; White, C. A. Bioactive Carbohydrates; Ellis Horwood, Ltd.: Chichester, West Sussex, 1983.
4. For concepts on the use of carbohydrates in synthesis, see: Hanessian, S. Total Synthesis of Natural Products. The Chiron Approach; Pergamon Press: Oxford, 1983. Hanessian, S.; Rancourt, G. Pure Appl. Chem. 1977, 49, 1201. Fraser-Reid, B.; Tom, T. F.; Sun, K. M. Organic Synthesis, Today and Tomorrow; Trost, B. M., Hutchinson, C. R., Eds.; Pergamon Press: Oxford, 1981. Inch, T. D. Tetrahedron 1984, 40, 3161. Bhat, K. L.; Chen, S. Y. ; Joullie, M. M. Heterocycles 1985, 23, 691.
5. Review: Masamune, S.; Bates, G. S.; Corcoran, J. W. Angew. Chem., Int. Ed. Engl. 1977, 16, 585. Macrolide Antibiotics; Omura, S., Ed.; Academic Press: Orlando, 1984.
6. The Chemistry of Antitumor Antibiotics; Remers, W. A., Ed.; Wiley: New York, 1979. See, for instance: Roush, W. R.; Straub, J. A. Tetrahedron Lett. 1986, 27, 3349. Smith, A. B., III; Rivero, R. A. J. Am. Chem. Soc. 1987. 109. 1272.
7. Suhadolnik, R. J. Nucleosides as Biological Probes; Wiley: New York. 1979.
8. Uemura, D.; Hirat, Y.; Naoki, H.; Iwashita, T. Tetrahedron Lett. 1981, 2781. Moore, R. E.; Bartolini, G. J. Am. Chem. Soc. 1981,103, 2491. Cha, I. K.; Christ, W. J.; Finan, J. M.; Fujioka, H.; Kishi, Y.; Klein, L. L.; Ko, S. S.; Leder, J.; Mc Whorther, W. W., Jr.; Pfaff, K. P. ; Yonaga, M.; Uemura, D.; Hirata. Y. J. Am. Chem. Soc. 1982. 104. 7369.
9. Reviews: (a) McGarvey, G. J.; Kimura, M.; Oh, T.; Williams, J. M. J. Carbohydr. Chem. 1984, 3, 125. Masamune, S.; Chay, W.; Petersen, J. S.; Sita, L. R. Angew. Chem., Int. Ed. Engl. 1985, 24,1. (c) Fraser-Reid, B. Acc. Chem. Res. 1985, 18, 347. (d) Jager, V.; Muller, I.; Schohe, R.; Frey, M.; Ehrler, R.; Hafele, B.; Schroter, D. Lect. Heterocycl. Chem. 1985, 8, 79. (e) Jurczak, J.; Pikul, S.; Bauer, T. Tetrahedron 1986, 42, 447. (f) Hauser, F. M.; Ellenberger, S. R. Chem. Rev. 1986, 86, 35. (g) Schmidt, R. R. Acc. Chem. Res. 1986, 19, 250. (h) Hoffmann, R. W. Angew. Chem., Int. Ed. Engl. 1987, 26, 480. (i) Danishefsky, S. J.; DeN-inno, M. P. Tetrahedron Lett. 1987, 26, 15. (j) Achmatowicz, O. Organic Synthesis, Today and Tomorrow; Trost, B. M., Hutchinson, C. R., Eds.; Pergamon Press: Oxford, 1981; p 307.
10. Selected and/or recent papers: (a) Suzuki, K.; Yuki, Y.; Mukaiyama, T. Chem. Lett. 1981, 1529. Mukaiyama, T.; Yuki, Y.; Suzuki, K. J. Carbohydr. Chem. 1982, 1169. Murakami, M.; Mukaiyama, T. J. Carbohydr. Chem. 1982, 1271. Mukaiyama, T.; Yamada, T.; Suzuki, K. J. Carbohydr. Chem. 1983, 5. Mukaiyama, T.; Tsuzuki, R.; Kato, J. J. Carbohydr. Chem. 1985, 837. Mukaiyama, T.; Yura, T.; Iwasawa, N. J. Carbohydr. Chem. 1985, 809. Fronza, G.; Fuganti, C.; Grasselli, P.; Marinoni, G. Tetrahedron Lett. 1979, 3883. Fronza, G.; Fuganti, C.; Grasselli, P.; Majori, L.; Pedrocchi-Fantoni, G.; Spreafico, F. J. Org. Chem. 1982, 47, 3289. Fronza, G.; Fuganti, C.; Grasselli, P.; Servi, S. J. Org. Chem. 1987, 52, 2086. (c) Vasella, A.; Voeffray, R. Helv. Chim. Acta 1982, 65, 1134. (d) DeShong, P.; Dicken, C. M.; Leginus, J. M.; Whittle, R. R. J. Am. Chem. Soc. 1984, 106, 5598. (e) Minami, N.; Ko, S. S.; Kishi, Y. J. Am. Chem. Soc. 1982,104, 1109. (f) Lee, A. W. M.; Martin, V. S.; Masamune, S.; Sharpless, K. B.; Walker, F. J. J. Am. Chem. Soc. 1982, 104, 3515. Katsuki, T.; Lee, A. W. M.; Ma, P.; Martin, V. S.; Masamune, S.; Sharpless, K. B.; Tuddenham, D.; Walker, F. J. J. Org. Chem. 1982, 47, 1373. Ma, P.; Martin, V. S.; Masamune, S.; Sharpless, K. B.; Viti, S. M. J. Carbohydr. Chem. 1982, 47, 1378. (g) Hanessian, S.; Sahoo, S. P.; Murray, P. J. Tetrahedron Lett. 1985, 26, 5623, 5627, and 5631. (h) Okamoto, S.; Shimazaki, T.; Kitano, Y.; Kobayashi, Y.; Sato, F. J. Chem. Soc., Chem. Commun. 1986, 1352. (i) Tamao, K.; Nakajima, T.; Sumiya, R.; Arai, H.; Higuchi, N.; Ito, Y. J. Am. Chem. Soc. 1986, 108, 6090. (j) Williams, D. K.; Klingleer, F. D. Tetrahedron Lett. 1987, 28, 869. (k) Pikul, S.; Raczko, J.; Anker, K.; Jurczak, J. J. Am. Chem. Soc. 1987, 109, 3981. (1) Roush, W. R.; Straub, J. A.; Brown, R. J. J. Org. Chem. 1987, 52, 5127. (m) Pearson, W. H.; Cheng, M. C. J. Carbohydr. Chem. 1987,52, 3176. (n) Solladie, G.; Hutt, J.; Frechou, C. Tetrahedron Lett. 1987, 28, 61 and 797. (o) Matteson, D. S.; Peterson, M. L. J. Org. Chem. 1987, 52, 5116. (p) Schreiber, S. L.; Goulet, M. T. J. Am. Chem. Soc. 1987, 109, 4718.
11. Reviews: see ref 2b and Dondoni, A.; Fantin, G.; Fogagnolo, M.; Mastellari, A. R.; Medici, A.; Negrini, E.; Pedrini, P. Gazz. Chim. Ital. 1988, 118, 211.
12. Dondoni, A.; Fantin, G.; Fogagnolo, M.; Medici, A.; Pedrini, P. J. Org. Chem. 1988, 53, 1748.
13. Altman, L. J.; Richheimer, S. L. Tetrahedron Lett. 1971, 4709. Meyers, A. I.; Munavu, R.; Durandetta, J. J. Org. Chem. 1972, 3929.
14. Mukaivama. T.; Suzuki. K.; Yamada, T. Chem. Lett. 1982. 929.
15. Servi, S. J. Org. Chem. 1985, 50, 5866.
16. Throughout the paper, the degree of diastereoselectivity is given as % ds, that is the percentage of the major diastereomer in the mixture. See, for instance: Seebach, D.; Helmchen, G.; Brown, A. C. “Synthesis of Enantiomerically Pure Compounds” in Modern Synthetic Methods 1986; Scheffold, R., Ed.; Springer-Verlag: Berlin, 1986; p 125.
17. The relative configuration is assigned as anti or syn according to the definition of Masamune (Masamune, S.; Ali, A.; Snitman, D. L.; Garvey, D. S. Angew. Chem., Int. Ed. Engl. 1980, 19, 557. Masamune, S.: Kaiho. T.; Garvey, D. S. J. Am. Chem. Soc. 1982. 104. 5521).
18. Cherest, M.; Felkin, H.; Prudent, N. Tetrahedron Lett. 1968, 2199. Anh, N. T. Ton. Curr. Chem. 1980. 88. 145.
19. For reviews and recent studies, see ref 10a and (a) Reetz, M. T. Angew. Chem., Int. Ed. Engl. 1984, 23, 556. Reetz, M. T.; Kesseler, K. J. Org. Chem. 1985, 50, 5435. Roush, W. R.; Adam, M. A.; Walts, A. E.; Harris, D. J. J. Am. Chem. Soc. 1986, 108, 3422. (c) Mead, K.; McDonald, T. L. J. Org. Chem. 1985. 50. 422.
20. Dondoni, A.; Fantin, G.; Fogagnolo, M.; Medici, A.; Pedrini, P. J. Org. Chem., accompanying note in this issue.
21. Recently Houk and co-workers have reported ab initio calculations supporting the Felkin-Anh model for asymmetric induction; Pad-don-Row, M. N.; Rondan, N. G.; Houk, K. N. J. Am. Chem. Soc. 1982, 104, 7162. Wu, Y. D. ; Houk, K. N. J. Org. Chem. 1987, 109, 906 and 908.
22. Dondoni, A.; Fantin, G.; Fogagnolo, M.; Medici, A.; Pedrini, P. Tetrahedron 1988. 44. 3215.
23. For a review on thiazole chemistry, see also: Metzger, A. I. The Chemistry of Heterocyclic Compounds. Thiazole and its Derivatives; Wiley: New York, 1979; Vol. 34.
24. An inconvenient exception occurs with 2-vinylthiazoles that lead to saturated aldehydes instead of,α,β-enals. See: Dondoni, A.; Fantin, G.; Fogagnolo, M.; Medici, A.; Pedrini, P. Tetrahedron 1988, 44, 2021.
25. Benzothiazole, which has been employed as a masked formyl group (Corey, E. J.; Boger, D. L. Tetrahedron Lett. 1978, 5), appears to be a less convenient auxiliary in our methodology since 2-(trimethyl-silyl)benzothiazole reacts sluggishly and in low selectivity with the aldehyde 2a (ref 2a) and the formyl deblocking (N-quaternization step) is more difficult. For a compilation of references of formyl and acyl anion synthons, see: Hase, T. A.; Koskimilo, J. K. Aldrichimica Acta 1981, 14, 73. See also ref 33 and 35 and references cited therein.
26. For earlier work on C-disaccharides, see: Danishefsky. S. J.; Maring, C. J.; Barbachyn, M. R.; Segmuller, B. E. J. Org. Chem. 1984, 49. 4564 and references cited therein.
27. Barton, D. H. R.; McCombie, S. W. J. Chem. Soc., Perkin Trans. I 1975, 1574. Reviews: Hartwig, W. Tetrahedron 1983, 39, 2609. Neuman, W. P. Synthesis 1987, 665.
28. See ref. 5a and Hanessian, S.; Delorne, D.; Tyler, P. G.; Demaily, G.; Charplens, Y. Current Trends in Organic Synthesis; Nozaki, H., Ed.; Pergamon: Oxford, 1983; p 205.
29. Fisher, E. Ber. Dtsch. Chem. Ges. 1889, 22, 2204. Kiliani, H. Ber. Dtsch. Chem. Ges, 1885, 18, 3066. Review: Hudson, C. S. Adv. Carbo-hydr. Chem. 1945, 1, 1.
30. Jurczak, J.; Pikul, S.; Bauer, T. Tetrahedron 1986, 42, 893.
31. Mukaiyama. T.; Suzuki. K.: Yamada. T. Chem. Lett. 1982, 929.
32. Heathcock, C. H.; Kiyooka, S.; Blumenkopf, T. A. J. Org. Chem. 1984, 49, 4214.
33. Wolfrom, M. L.; Hanessian, S. J. Org. Chem. 1962, 26. 1800.
34. Howart, G. B.; Lance, D. G.; Szarek, W. A.; Jones, J. K. N. Can. J. Chem. 1969, 47, 75.
35. Danishefsky, S. J.; Pearson, W. H.; Harvey, D. F.; Maring, C. J.; Springer, J. P. J. Am. Chem. Soc. 1985, 107, 1256.