Synthesis of the Carbon Skeleton of the Herbicidins via a Temporary Silaketal Tether

Synlett

Volumn 1996, Issue 7, 1996, Pages 679-681

  Fairbanks, Antony J ^a,b   Perrin, Elisabeth ^a   Sinaÿ, Pierre ^a  

^a ECOLE NORMALE SUPÉRIEURE   (France)

^b UNIVERSITY OF CAMBRIDGE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 1542607455     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-5559     Document Type: Article

References (32)

1. Herbicidins A and B: Arai, M.; Haneishi, T.; Kitahara, N.; Enokita, R.; Kawakubo, K.; Kondo, Y. J. Antibiot. 1976, 29, 863; Haneishi, T.; Terahara, A.; Kayamori, H.; Yabe, J.; Arai, M. J. Antibiot. 1976, 29, 870; Herbicidins C and E: Takiguchi, Y.; Yoshikawa, H.; Terahara, A.; Torikata, A.; Terao, M. J. Antibiot. 1979, 32, 857; Herbicidins F and G: Takiguchi, Y.; Yoshikawa, H.; Terahara, A.; Torikata, A.; Terao, M. J. Antibiot. 1979, 32, 862. The structure of Herbicidin D has not yet been firmly established.
2. Herbicidins A and B: Arai, M.; Haneishi, T.; Kitahara, N.; Enokita, R.; Kawakubo, K.; Kondo, Y. J. Antibiot. 1976, 29, 863; Haneishi, T.; Terahara, A.; Kayamori, H.; Yabe, J.; Arai, M. J. Antibiot. 1976, 29, 870; Herbicidins C and E: Takiguchi, Y.; Yoshikawa, H.; Terahara, A.; Torikata, A.; Terao, M. J. Antibiot. 1979, 32, 857; Herbicidins F and G: Takiguchi, Y.; Yoshikawa, H.; Terahara, A.; Torikata, A.; Terao, M. J. Antibiot. 1979, 32, 862. The structure of Herbicidin D has not yet been firmly established.
3. Herbicidins A and B: Arai, M.; Haneishi, T.; Kitahara, N.; Enokita, R.; Kawakubo, K.; Kondo, Y. J. Antibiot. 1976, 29, 863; Haneishi, T.; Terahara, A.; Kayamori, H.; Yabe, J.; Arai, M. J. Antibiot. 1976, 29, 870; Herbicidins C and E: Takiguchi, Y.; Yoshikawa, H.; Terahara, A.; Torikata, A.; Terao, M. J. Antibiot. 1979, 32, 857; Herbicidins F and G: Takiguchi, Y.; Yoshikawa, H.; Terahara, A.; Torikata, A.; Terao, M. J. Antibiot. 1979, 32, 862. The structure of Herbicidin D has not yet been firmly established.
4. Herbicidins A and B: Arai, M.; Haneishi, T.; Kitahara, N.; Enokita, R.; Kawakubo, K.; Kondo, Y. J. Antibiot. 1976, 29, 863; Haneishi, T.; Terahara, A.; Kayamori, H.; Yabe, J.; Arai, M. J. Antibiot. 1976, 29, 870; Herbicidins C and E: Takiguchi, Y.; Yoshikawa, H.; Terahara, A.; Torikata, A.; Terao, M. J. Antibiot. 1979, 32, 857; Herbicidins F and G: Takiguchi, Y.; Yoshikawa, H.; Terahara, A.; Torikata, A.; Terao, M. J. Antibiot. 1979, 32, 862. The structure of Herbicidin D has not yet been firmly established.
5. Terahara, A.; Haneishi, T.; Arai, M.; Hata, T.; Kuwano, H.; Tamura, C. J. Antibiot., 1982, 35, 1171.
6. Dai, X.; Li, G.; Wu, D.; Lu, D.; Wang, H.; Li, Z.; Zhou, L.; Chen, X.; Chen, W. Faming Zhuanli Shenquing Gongkai Shuomingshu CN 87100250; Chem. Abstr., 1989, 111, 230661f.
7. Herbicidins A and B show selective toxicity towards dicotyledonous plants and also inhibit Xanthomonas oryzae a cause of rice leaf blight. See Reference 2.
8. For a review of the chemistry and synthesis of C-glycosides see: Levy, D.E.; Tang, C. The Chemistry of C-glycosides, Tetrahedron Organic Chemistry Series, Pergamon, 1995.
9. Newcombe, N.J.; Mahon, M.F.; Molloy, K.C.; Alker, D.; Gallagher, T. J. Am. Chem. Soc. 1993, 115, 6430. Cox, P.; Mahon, M.F.; Molloy, K.C.; Lister, S.; Gallagher, T. Tetrahedron Lett. 1989, 50, 2437. Cox, P.; Mahon, M.F.; Molloy, K.C.; Lister, S.; Gallagher, T. Tetrahedron Lett. 1988, 29, 1993. For a Lewis acid mediated approach by the same research group see Cox, P.; Griffin, A.M.; Newcombe, N.J.; Lister, S.; Ramsay, M.V.J.; Alker, D.; Gallagher, T. J. Chem. Soc., Perkin Trans. 1 1994, 1443. and references therein.
10. Newcombe, N.J.; Mahon, M.F.; Molloy, K.C.; Alker, D.; Gallagher, T. J. Am. Chem. Soc. 1993, 115, 6430. Cox, P.; Mahon, M.F.; Molloy, K.C.; Lister, S.; Gallagher, T. Tetrahedron Lett. 1989, 50, 2437. Cox, P.; Mahon, M.F.; Molloy, K.C.; Lister, S.; Gallagher, T. Tetrahedron Lett. 1988, 29, 1993. For a Lewis acid mediated approach by the same research group see Cox, P.; Griffin, A.M.; Newcombe, N.J.; Lister, S.; Ramsay, M.V.J.; Alker, D.; Gallagher, T. J. Chem. Soc., Perkin Trans. 1 1994, 1443. and references therein.
11. Newcombe, N.J.; Mahon, M.F.; Molloy, K.C.; Alker, D.; Gallagher, T. J. Am. Chem. Soc. 1993, 115, 6430. Cox, P.; Mahon, M.F.; Molloy, K.C.; Lister, S.; Gallagher, T. Tetrahedron Lett. 1989, 50, 2437. Cox, P.; Mahon, M.F.; Molloy, K.C.; Lister, S.; Gallagher, T. Tetrahedron Lett. 1988, 29, 1993. For a Lewis acid mediated approach by the same research group see Cox, P.; Griffin, A.M.; Newcombe, N.J.; Lister, S.; Ramsay, M.V.J.; Alker, D.; Gallagher, T. J. Chem. Soc., Perkin Trans. 1 1994, 1443. and references therein.
12. Newcombe, N.J.; Mahon, M.F.; Molloy, K.C.; Alker, D.; Gallagher, T. J. Am. Chem. Soc. 1993, 115, 6430. Cox, P.; Mahon, M.F.; Molloy, K.C.; Lister, S.; Gallagher, T. Tetrahedron Lett. 1989, 50, 2437. Cox, P.; Mahon, M.F.; Molloy, K.C.; Lister, S.; Gallagher, T. Tetrahedron Lett. 1988, 29, 1993. For a Lewis acid mediated approach by the same research group see Cox, P.; Griffin, A.M.; Newcombe, N.J.; Lister, S.; Ramsay, M.V.J.; Alker, D.; Gallagher, T. J. Chem. Soc., Perkin Trans. 1 1994, 1443. and references therein.
13. Bearder, J.R.; Dewis, M.L.; Whiting, D.A. Synlett 1993, 805; Bearder, J.R.; Dewis, M.L.; Whiting, D.A. J. Chem. Soc., Perkin Trans. 1 1995, 227.
14. Bearder, J.R.; Dewis, M.L.; Whiting, D.A. Synlett 1993, 805; Bearder, J.R.; Dewis, M.L.; Whiting, D.A. J. Chem. Soc., Perkin Trans. 1 1995, 227.
15. Emery, F.; Vogel, P. Tetrahedron Lett. 1993, 26, 4209; Emery, F.; Vogel, P. J. Org. Chem., 1995, 60, 5843.
16. Emery, F.; Vogel, P. Tetrahedron Lett. 1993, 26, 4209; Emery, F.; Vogel, P. J. Org. Chem., 1995, 60, 5843.
17. For other examples of this approach to C-disaccharide synthesis see: Xin, Y.C.; Mallet, J.-M.; Sinaÿ, P. J. Chem. Soc., Chem. Commun., 1993, 864; Vauzeilles, B.; Cravo, D.; Mallet, J.-M.; Sinaÿ, P. Synlett, 1993, 522; Chénedé, A.; Perrin, E.; Rekaï, E.; Sinaÿ, P. Synlett, 1994, 420.
18. For other examples of this approach to C-disaccharide synthesis see: Xin, Y.C.; Mallet, J.-M.; Sinaÿ, P. J. Chem. Soc., Chem. Commun., 1993, 864; Vauzeilles, B.; Cravo, D.; Mallet, J.-M.; Sinaÿ, P. Synlett, 1993, 522; Chénedé, A.; Perrin, E.; Rekaï, E.; Sinaÿ, P. Synlett, 1994, 420.
19. For other examples of this approach to C-disaccharide synthesis see: Xin, Y.C.; Mallet, J.-M.; Sinaÿ, P. J. Chem. Soc., Chem. Commun., 1993, 864; Vauzeilles, B.; Cravo, D.; Mallet, J.-M.; Sinaÿ, P. Synlett, 1993, 522; Chénedé, A.; Perrin, E.; Rekaï, E.; Sinaÿ, P. Synlett, 1994, 420.
20. For a review of silicon based methods for tethering see: Bols, M.; Skrydstrup, T. Chem. Rev. 1995, 95, 1253.
21. Geise, B. Radicals in Organic Synthesis: Formation of Carbon-Carbon Bonds; Pergamon: Oxford, 1986; p 61.
22. This material is actually commercially available. The Aldrich 1995 catalogue price for 8 is £261.20 for 100g, as compared to £12.60 for 100g of D-xylose 7.
23. Cooke, N.G.; Jones, D.A.; Whiting, A. Tetrahedron 1992, 48, 9553.
24. 5 requires: C, 40.69; H, 5.12).
25. 4 requires: C, 55.80; H, 7.02).
26. David, S.; Malleron, A.; Dini, C. Carbohydr. Res. 1989, 188, 193.
27. 5Se requires: C, 62.61; H, 5.27).
28. 4), filtered, the solvent removed and the residue dried in vacuuo. This crude material was then used immediately for subsequent cyclisation.
29. 9 requires: C, 66.35; H, 6.66).
30. trans 1 Hz). This cis stereochemistry was confirmed for 4 by n.O.e. experiments where a 5% enhancement was observed for H-4 upon irradiation of H-3 (an identical enhancement to that observed between H-1 and H-2). No enhancement of H-5 or H-5′ was observed upon irradiation of H-3.
31. 7,8 10 Hz), 5.25 (1H, d, H-3), 5.62 (1H, s, CHPh), 5.94 (1H, d, H-1), 7.25-7.55 (10H, m, Ar).
32. 7,8 8 Hz), 5.61 (1H, s, CHPh), 5.98 (1H, d, H-1), 7.25-7.55 (10H, m, Ar).