A short synthesis of the bicyclic core of the zaragozic acids

Tetrahedron Letters

Volumn 39, Issue 43, 1998, Pages 7853-7856

  Fraisse, Pierre ^a   Hanna, Issam ^a   Lallemand, Jean Yves ^a  

^a LABORATOIRE DE SYNTHÈSE ORGANIQUE   (France)

Author keywords

D xylofuranuronic acid; (R) glyceraldehyde acetonide; Aldol reaction; Zaragozic Acids

Indexed keywords

ZARAGOZIC ACID A; ZARAGOZIC ACID C;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; DRUG STRUCTURE; DRUG SYNTHESIS;

EID: 0032558631     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01726-2     Document Type: Article

References (32)

1. 1. For a review of the chemistry and biology of the zaragozic acids (squalestatins) see: Nadin, A.; Nicolaou, K. C. Angew. chem. Int. Ed. Engl. 1996, 35, 1622-1656. For more recent approaches see: Hegde, S. G.; Myles, D. C. Tetrahedron Let. 1997, 38, 4329-4332. Xu, Y.; Johnson, C. R. Tetrahedron Let. 1997, 38, 1117-1120. Paterson, I.; Feßner, K.; Finaly, M. R. V.; Jacobs, M. F. Tetrahedron Let. 1997, 38, 4301-4304. Ito, H.; Matsumoto, M.; Yoshizawa, T.; Takao, K.; Kobayashi, S. Tetrahedron et. 1997, 38, 9009-9012. Brogan, J. B.; Zercher, C. K. Tetrahedron Let. 1998, 39, 1691-1694. Kataoka, O.; Kitagaki, S.; Watanabe, N.; Kobayashi, J.; Nakamura, S.; Shiro, M.; Hashimoto, S. Tetrahedron Let. 1998, 39, 2371-2374.
2. 1. For a review of the chemistry and biology of the zaragozic acids (squalestatins) see: Nadin, A.; Nicolaou, K. C. Angew. chem. Int. Ed. Engl. 1996, 35, 1622-1656. For more recent approaches see: Hegde, S. G.; Myles, D. C. Tetrahedron Let. 1997, 38, 4329-4332. Xu, Y.; Johnson, C. R. Tetrahedron Let. 1997, 38, 1117-1120. Paterson, I.; Feßner, K.; Finaly, M. R. V.; Jacobs, M. F. Tetrahedron Let. 1997, 38, 4301-4304. Ito, H.; Matsumoto, M.; Yoshizawa, T.; Takao, K.; Kobayashi, S. Tetrahedron et. 1997, 38, 9009-9012. Brogan, J. B.; Zercher, C. K. Tetrahedron Let. 1998, 39, 1691-1694. Kataoka, O.; Kitagaki, S.; Watanabe, N.; Kobayashi, J.; Nakamura, S.; Shiro, M.; Hashimoto, S. Tetrahedron Let. 1998, 39, 2371-2374.
3. 1. For a review of the chemistry and biology of the zaragozic acids (squalestatins) see: Nadin, A.; Nicolaou, K. C. Angew. chem. Int. Ed. Engl. 1996, 35, 1622-1656. For more recent approaches see: Hegde, S. G.; Myles, D. C. Tetrahedron Let. 1997, 38, 4329-4332. Xu, Y.; Johnson, C. R. Tetrahedron Let. 1997, 38, 1117-1120. Paterson, I.; Feßner, K.; Finaly, M. R. V.; Jacobs, M. F. Tetrahedron Let. 1997, 38, 4301-4304. Ito, H.; Matsumoto, M.; Yoshizawa, T.; Takao, K.; Kobayashi, S. Tetrahedron et. 1997, 38, 9009-9012. Brogan, J. B.; Zercher, C. K. Tetrahedron Let. 1998, 39, 1691-1694. Kataoka, O.; Kitagaki, S.; Watanabe, N.; Kobayashi, J.; Nakamura, S.; Shiro, M.; Hashimoto, S. Tetrahedron Let. 1998, 39, 2371-2374.
4. 1. For a review of the chemistry and biology of the zaragozic acids (squalestatins) see: Nadin, A.; Nicolaou, K. C. Angew. chem. Int. Ed. Engl. 1996, 35, 1622-1656. For more recent approaches see: Hegde, S. G.; Myles, D. C. Tetrahedron Let. 1997, 38, 4329-4332. Xu, Y.; Johnson, C. R. Tetrahedron Let. 1997, 38, 1117-1120. Paterson, I.; Feßner, K.; Finaly, M. R. V.; Jacobs, M. F. Tetrahedron Let. 1997, 38, 4301-4304. Ito, H.; Matsumoto, M.; Yoshizawa, T.; Takao, K.; Kobayashi, S. Tetrahedron et. 1997, 38, 9009-9012. Brogan, J. B.; Zercher, C. K. Tetrahedron Let. 1998, 39, 1691-1694. Kataoka, O.; Kitagaki, S.; Watanabe, N.; Kobayashi, J.; Nakamura, S.; Shiro, M.; Hashimoto, S. Tetrahedron Let. 1998, 39, 2371-2374.
5. 1. For a review of the chemistry and biology of the zaragozic acids (squalestatins) see: Nadin, A.; Nicolaou, K. C. Angew. chem. Int. Ed. Engl. 1996, 35, 1622-1656. For more recent approaches see: Hegde, S. G.; Myles, D. C. Tetrahedron Let. 1997, 38, 4329-4332. Xu, Y.; Johnson, C. R. Tetrahedron Let. 1997, 38, 1117-1120. Paterson, I.; Feßner, K.; Finaly, M. R. V.; Jacobs, M. F. Tetrahedron Let. 1997, 38, 4301-4304. Ito, H.; Matsumoto, M.; Yoshizawa, T.; Takao, K.; Kobayashi, S. Tetrahedron et. 1997, 38, 9009-9012. Brogan, J. B.; Zercher, C. K. Tetrahedron Let. 1998, 39, 1691-1694. Kataoka, O.; Kitagaki, S.; Watanabe, N.; Kobayashi, J.; Nakamura, S.; Shiro, M.; Hashimoto, S. Tetrahedron Let. 1998, 39, 2371-2374.
6. 1. For a review of the chemistry and biology of the zaragozic acids (squalestatins) see: Nadin, A.; Nicolaou, K. C. Angew. chem. Int. Ed. Engl. 1996, 35, 1622-1656. For more recent approaches see: Hegde, S. G.; Myles, D. C. Tetrahedron Let. 1997, 38, 4329-4332. Xu, Y.; Johnson, C. R. Tetrahedron Let. 1997, 38, 1117-1120. Paterson, I.; Feßner, K.; Finaly, M. R. V.; Jacobs, M. F. Tetrahedron Let. 1997, 38, 4301-4304. Ito, H.; Matsumoto, M.; Yoshizawa, T.; Takao, K.; Kobayashi, S. Tetrahedron et. 1997, 38, 9009-9012. Brogan, J. B.; Zercher, C. K. Tetrahedron Let. 1998, 39, 1691-1694. Kataoka, O.; Kitagaki, S.; Watanabe, N.; Kobayashi, J.; Nakamura, S.; Shiro, M.; Hashimoto, S. Tetrahedron Let. 1998, 39, 2371-2374.
7. 1. For a review of the chemistry and biology of the zaragozic acids (squalestatins) see: Nadin, A.; Nicolaou, K. C. Angew. chem. Int. Ed. Engl. 1996, 35, 1622-1656. For more recent approaches see: Hegde, S. G.; Myles, D. C. Tetrahedron Let. 1997, 38, 4329-4332. Xu, Y.; Johnson, C. R. Tetrahedron Let. 1997, 38, 1117-1120. Paterson, I.; Feßner, K.; Finaly, M. R. V.; Jacobs, M. F. Tetrahedron Let. 1997, 38, 4301-4304. Ito, H.; Matsumoto, M.; Yoshizawa, T.; Takao, K.; Kobayashi, S. Tetrahedron et. 1997, 38, 9009-9012. Brogan, J. B.; Zercher, C. K. Tetrahedron Let. 1998, 39, 1691-1694. Kataoka, O.; Kitagaki, S.; Watanabe, N.; Kobayashi, J.; Nakamura, S.; Shiro, M.; Hashimoto, S. Tetrahedron Let. 1998, 39, 2371-2374.
8. 2. Nicolaou, K. C.; Nadin, A.; Leresche, J. E.; Yue, E. W.; La Greca, S. Angew. chem. Int. Ed. Engl. 1994, 33, 2190-2191. Stoermer, D.; Caron, S.; Heathcock, C. H. J. Org. Chem. 1996, 61, 9115-9125. Caron, S.; Stoermer, D.; Mapp, A. K.; Heathcock, C. H. J. Org. Chem. 1996, 61, 9126-9134.
9. 2. Nicolaou, K. C.; Nadin, A.; Leresche, J. E.; Yue, E. W.; La Greca, S. Angew. chem. Int. Ed. Engl. 1994, 33, 2190-2191. Stoermer, D.; Caron, S.; Heathcock, C. H. J. Org. Chem. 1996, 61, 9115-9125. Caron, S.; Stoermer, D.; Mapp, A. K.; Heathcock, C. H. J. Org. Chem. 1996, 61, 9126-9134.
10. 2. Nicolaou, K. C.; Nadin, A.; Leresche, J. E.; Yue, E. W.; La Greca, S. Angew. chem. Int. Ed. Engl. 1994, 33, 2190-2191. Stoermer, D.; Caron, S.; Heathcock, C. H. J. Org. Chem. 1996, 61, 9115-9125. Caron, S.; Stoermer, D.; Mapp, A. K.; Heathcock, C. H. J. Org. Chem. 1996, 61, 9126-9134.
11. 3. Evans, D. A.; Barrow, J. C.; Leighton, J. L.; Robichaud, A. J.; Sefkow, M. J. Am. Chem. Soc. 1994, 116, 12111-12112. Carreira, E. M.; Du Bois, J. J. Am. Chem. Soc. 1995, 117, 8106-8125. Sato, H.; Nakamura, S.; Watanabe, N.; Hashimoto, S. Synlett, 1997, 451-454. Armstrong, A.; Jones, L. H.; Barsanti, P. A. Tetrahedron Let. 1998, 39, 3337-3340.
12. 3. Evans, D. A.; Barrow, J. C.; Leighton, J. L.; Robichaud, A. J.; Sefkow, M. J. Am. Chem. Soc. 1994, 116, 12111-12112. Carreira, E. M.; Du Bois, J. J. Am. Chem. Soc. 1995, 117, 8106-8125. Sato, H.; Nakamura, S.; Watanabe, N.; Hashimoto, S. Synlett, 1997, 451-454. Armstrong, A.; Jones, L. H.; Barsanti, P. A. Tetrahedron Let. 1998, 39, 3337-3340.
13. 3. Evans, D. A.; Barrow, J. C.; Leighton, J. L.; Robichaud, A. J.; Sefkow, M. J. Am. Chem. Soc. 1994, 116, 12111-12112. Carreira, E. M.; Du Bois, J. J. Am. Chem. Soc. 1995, 117, 8106-8125. Sato, H.; Nakamura, S.; Watanabe, N.; Hashimoto, S. Synlett, 1997, 451-454. Armstrong, A.; Jones, L. H.; Barsanti, P. A. Tetrahedron Let. 1998, 39, 3337-3340.
14. 3. Evans, D. A.; Barrow, J. C.; Leighton, J. L.; Robichaud, A. J.; Sefkow, M. J. Am. Chem. Soc. 1994, 116, 12111-12112. Carreira, E. M.; Du Bois, J. J. Am. Chem. Soc. 1995, 117, 8106-8125. Sato, H.; Nakamura, S.; Watanabe, N.; Hashimoto, S. Synlett, 1997, 451-454. Armstrong, A.; Jones, L. H.; Barsanti, P. A. Tetrahedron Let. 1998, 39, 3337-3340.
15. 5 in methanol with a catalytic amount of Amberlite IR ion exchange resin for 24 h, followed by the the protection of the secondary alcohol as its methoxymethyl ether.
16. 5. Dhavale, D. D.; Tagliavini, E.; Trombini, C.; Umani-Ronchi, A. J. Org. Chem. 1989, 54, 4100-4105.
17. 6. Prepared from D-mannitol according to the litterature procedure: Schmid, C.; Bryant, J. D. Org. Synth. 1995, 72, 6-13.
18. 7. For the formation of carbon-carbon bonds at C4 of the furanose ring bearing an alkoxy group at C3 see: a) from an aldehyde at C4 via enamine and enol acetate derivatives: Secrist, J. A.; Winter, W. J. J. Am. Chem. Soc. 1978, 100, 2554-2555; by Cannizzaro reaction with formaldehyde: Jones, G. H.; Tanguchi, D. T.; Moffat, J. G. J. Org. Chem. 1979, 44, 1309-1317. Gurjar, M. K.; Das, S. K.; Sadalapure, K. S. Tetrahedron Let. 1995, 36, 1933-1936.
19. 7. For the formation of carbon-carbon bonds at C4 of the furanose ring bearing an alkoxy group at C3 see: a) from an aldehyde at C4 via enamine and enol acetate derivatives: Secrist, J. A.; Winter, W. J. J. Am. Chem. Soc. 1978, 100, 2554-2555; by Cannizzaro reaction with formaldehyde: Jones, G. H.; Tanguchi, D. T.; Moffat, J. G. J. Org. Chem. 1979, 44, 1309-1317. Gurjar, M. K.; Das, S. K.; Sadalapure, K. S. Tetrahedron Let. 1995, 36, 1933-1936.
20. 7. For the formation of carbon-carbon bonds at C4 of the furanose ring bearing an alkoxy group at C3 see: a) from an aldehyde at C4 via enamine and enol acetate derivatives: Secrist, J. A.; Winter, W. J. J. Am. Chem. Soc. 1978, 100, 2554-2555; by Cannizzaro reaction with formaldehyde: Jones, G. H.; Tanguchi, D. T.; Moffat, J. G. J. Org. Chem. 1979, 44, 1309-1317. Gurjar, M. K.; Das, S. K.; Sadalapure, K. S. Tetrahedron Let. 1995, 36, 1933-1936.
21. b) from ester at C4 via the Claisen rearrangement of the enolate: Ireland, R. E.; Norbeck, D. W. J. Am. Chem. Soc. 1985, 107, 3279-3285. McVinish, L. M.; Rizzacasa, M. A. Tetrahedron Let. 1994, 35, 923-926.
22. b) from ester at C4 via the Claisen rearrangement of the enolate: Ireland, R. E.; Norbeck, D. W. J. Am. Chem. Soc. 1985, 107, 3279-3285. McVinish, L. M.; Rizzacasa, M. A. Tetrahedron Let. 1994, 35, 923-926.
23. 8. Handa, S.; Tsang, R.; McPhail, A. T.; Fraser-Reid, B. J. Org. Chem. 1987, 52, 3489-3491 and references cited therein.
24. 9. Attempts to achieve the aldol reaction via enol acetate, enamine or silyl ketene acetal derivatives of 2 were unsuccessful.
25. 10. Dess, D. B.; Martin, J. C. J. Am. Chem. Soc. 1991, 113, 7277-7287 Ireland, R. E.; Liu, L. J. Org. Chem. 1993, 58, 2899.
26. 10. Dess, D. B.; Martin, J. C. J. Am. Chem. Soc. 1991, 113, 7277-7287 Ireland, R. E.; Liu, L. J. Org. Chem. 1993, 58, 2899.
27. 3, acetates) ppm.
28. 12. See for examples: Paterson, I.; Feßner, K.; Finaly, M. R. V.; Jacobs, M. F. Tetrahedron Let. 1996, 37, 8803-8806. Xu, Y.; Johnson, C. R. Tetrahedron Let. 1997, 38, 1117-1120. Hegde, S. G.; Myles, D. C. Tetrahedron 1997, 53, 11179-11190. Armstrong, A.; Jones, L. H.; Barsanti, P. A. Tetrahedron Let. 1998, 39, 3337-3340.
29. 12. See for examples: Paterson, I.; Feßner, K.; Finaly, M. R. V.; Jacobs, M. F. Tetrahedron Let. 1996, 37, 8803-8806. Xu, Y.; Johnson, C. R. Tetrahedron Let. 1997, 38, 1117-1120. Hegde, S. G.; Myles, D. C. Tetrahedron 1997, 53, 11179-11190. Armstrong, A.; Jones, L. H.; Barsanti, P. A. Tetrahedron Let. 1998, 39, 3337-3340.
30. 12. See for examples: Paterson, I.; Feßner, K.; Finaly, M. R. V.; Jacobs, M. F. Tetrahedron Let. 1996, 37, 8803-8806. Xu, Y.; Johnson, C. R. Tetrahedron Let. 1997, 38, 1117-1120. Hegde, S. G.; Myles, D. C. Tetrahedron 1997, 53, 11179-11190. Armstrong, A.; Jones, L. H.; Barsanti, P. A. Tetrahedron Let. 1998, 39, 3337-3340.
31. 12. See for examples: Paterson, I.; Feßner, K.; Finaly, M. R. V.; Jacobs, M. F. Tetrahedron Let. 1996, 37, 8803-8806. Xu, Y.; Johnson, C. R. Tetrahedron Let. 1997, 38, 1117-1120. Hegde, S. G.; Myles, D. C. Tetrahedron 1997, 53, 11179-11190. Armstrong, A.; Jones, L. H.; Barsanti, P. A. Tetrahedron Let. 1998, 39, 3337-3340.
32. 13. For a review see: David, S.; Hanessian, S. Tetrahedron, 1985, 41, 643-663.