Stereoselective synthesis of the published structure of synargentolide A and of one of its stereoisomers

Arkivoc

Volumn 2005, Issue 9, 2005, Pages 175-188

  García Fortanet, Jorge ^a   Murga, Juan ^a   Carda, Miguel ^a   Marco, J Alberto ^b  

^a UNIVERSITAT JAUME I   (Spain)

^b UNIVERSITY OF VALENCIA   (Spain)

Author keywords

Asymmetric allylboration; Asymmetric dihydroxylation; Ring closing metathesis; Synargentolide A

Indexed keywords

LACTONE DERIVATIVE; NATURAL PRODUCT; SYNARGENTOLIDE A; UNCLASSIFIED DRUG;

ALLYLATION; ARTICLE; ASYMMETRIC SYNTHESIS; DATA ANALYSIS; DRUG STRUCTURE; DRUG SYNTHESIS; RING CLOSING METATHESIS; SPECTROSCOPY; STEREOCHEMISTRY; STEREOISOMERISM; STRUCTURE ANALYSIS;

EID: 17844406140     PISSN: 14246376     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (39)

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10. For studies on the biological properties of lactones containing a 6-substituted 5,6-dihydropyran-2-one moiety, see, for example: (a) Stampwala, S. S.; Bunge, R. H.; Hurley, T. R.; Willmer, N. E.; Brankiewicz, A. J.; Steinman, C.E.; Smitka, T. A.; French, J. C. J. Antibiot. 1983, 36, 1601. (b) Davis, R. M.; Richard, J. L. Dev. Food Sci. 1984, 8, 315. (c) Nagashima, H.; Nakamura, K.; Goto, T. Biochem. Biophys. Res. Commun. 2001, 287, 829. (d) Raoelison, G. E.; Terreaux, C.; Queiroz, E. F.; Zsila, F.; Simonyi, M.; Antus, S.; Randriantsoa, A.; Hostettmann, K. Helv. Chim. Acta 2001, 84, 3470. (e) Kalesse, M.; Christmann, M. Synthesis 2002, 981-1003. (f) Lewy, D. S.; Gauss, C.-M.; Soenen, D. R.; Boger, D. L. Curr. Med. Chem. 2002, 9, 2005. (g) Larsen, A. K.; Escargueil, A. E.; Skladanowski, A. Pharmacol. Ther. 2003, 99, 167-181. (h) Richetti, A.; Cavallaro, A.; Ainis, T.; Fimiani, V. Immunopharmacol. Immunotoxicol. 2003, 25, 441.
11. For studies on the biological properties of lactones containing a 6-substituted 5,6-dihydropyran-2-one moiety, see, for example: (a) Stampwala, S. S.; Bunge, R. H.; Hurley, T. R.; Willmer, N. E.; Brankiewicz, A. J.; Steinman, C.E.; Smitka, T. A.; French, J. C. J. Antibiot. 1983, 36, 1601. (b) Davis, R. M.; Richard, J. L. Dev. Food Sci. 1984, 8, 315. (c) Nagashima, H.; Nakamura, K.; Goto, T. Biochem. Biophys. Res. Commun. 2001, 287, 829. (d) Raoelison, G. E.; Terreaux, C.; Queiroz, E. F.; Zsila, F.; Simonyi, M.; Antus, S.; Randriantsoa, A.; Hostettmann, K. Helv. Chim. Acta 2001, 84, 3470. (e) Kalesse, M.; Christmann, M. Synthesis 2002, 981-1003. (f) Lewy, D. S.; Gauss, C.-M.; Soenen, D. R.; Boger, D. L. Curr. Med. Chem. 2002, 9, 2005. (g) Larsen, A. K.; Escargueil, A. E.; Skladanowski, A. Pharmacol. Ther. 2003, 99, 167-181. (h) Richetti, A.; Cavallaro, A.; Ainis, T.; Fimiani, V. Immunopharmacol. Immunotoxicol. 2003, 25, 441.
12. For studies on the biological properties of lactones containing a 6-substituted 5,6-dihydropyran-2-one moiety, see, for example: (a) Stampwala, S. S.; Bunge, R. H.; Hurley, T. R.; Willmer, N. E.; Brankiewicz, A. J.; Steinman, C.E.; Smitka, T. A.; French, J. C. J. Antibiot. 1983, 36, 1601. (b) Davis, R. M.; Richard, J. L. Dev. Food Sci. 1984, 8, 315. (c) Nagashima, H.; Nakamura, K.; Goto, T. Biochem. Biophys. Res. Commun. 2001, 287, 829. (d) Raoelison, G. E.; Terreaux, C.; Queiroz, E. F.; Zsila, F.; Simonyi, M.; Antus, S.; Randriantsoa, A.; Hostettmann, K. Helv. Chim. Acta 2001, 84, 3470. (e) Kalesse, M.; Christmann, M. Synthesis 2002, 981-1003. (f) Lewy, D. S.; Gauss, C.-M.; Soenen, D. R.; Boger, D. L. Curr. Med. Chem. 2002, 9, 2005. (g) Larsen, A. K.; Escargueil, A. E.; Skladanowski, A. Pharmacol. Ther. 2003, 99, 167-181. (h) Richetti, A.; Cavallaro, A.; Ainis, T.; Fimiani, V. Immunopharmacol. Immunotoxicol. 2003, 25, 441.
13. For studies on the biological properties of lactones containing a 6-substituted 5,6-dihydropyran-2-one moiety, see, for example: (a) Stampwala, S. S.; Bunge, R. H.; Hurley, T. R.; Willmer, N. E.; Brankiewicz, A. J.; Steinman, C.E.; Smitka, T. A.; French, J. C. J. Antibiot. 1983, 36, 1601. (b) Davis, R. M.; Richard, J. L. Dev. Food Sci. 1984, 8, 315. (c) Nagashima, H.; Nakamura, K.; Goto, T. Biochem. Biophys. Res. Commun. 2001, 287, 829. (d) Raoelison, G. E.; Terreaux, C.; Queiroz, E. F.; Zsila, F.; Simonyi, M.; Antus, S.; Randriantsoa, A.; Hostettmann, K. Helv. Chim. Acta 2001, 84, 3470. (e) Kalesse, M.; Christmann, M. Synthesis 2002, 981-1003. (f) Lewy, D. S.; Gauss, C.-M.; Soenen, D. R.; Boger, D. L. Curr. Med. Chem. 2002, 9, 2005. (g) Larsen, A. K.; Escargueil, A. E.; Skladanowski, A. Pharmacol. Ther. 2003, 99, 167-181. (h) Richetti, A.; Cavallaro, A.; Ainis, T.; Fimiani, V. Immunopharmacol. Immunotoxicol. 2003, 25, 441.
14. For studies on the biological properties of lactones containing a 6-substituted 5,6-dihydropyran-2-one moiety, see, for example: (a) Stampwala, S. S.; Bunge, R. H.; Hurley, T. R.; Willmer, N. E.; Brankiewicz, A. J.; Steinman, C.E.; Smitka, T. A.; French, J. C. J. Antibiot. 1983, 36, 1601. (b) Davis, R. M.; Richard, J. L. Dev. Food Sci. 1984, 8, 315. (c) Nagashima, H.; Nakamura, K.; Goto, T. Biochem. Biophys. Res. Commun. 2001, 287, 829. (d) Raoelison, G. E.; Terreaux, C.; Queiroz, E. F.; Zsila, F.; Simonyi, M.; Antus, S.; Randriantsoa, A.; Hostettmann, K. Helv. Chim. Acta 2001, 84, 3470. (e) Kalesse, M.; Christmann, M. Synthesis 2002, 981-1003. (f) Lewy, D. S.; Gauss, C.-M.; Soenen, D. R.; Boger, D. L. Curr. Med. Chem. 2002, 9, 2005. (g) Larsen, A. K.; Escargueil, A. E.; Skladanowski, A. Pharmacol. Ther. 2003, 99, 167-181. (h) Richetti, A.; Cavallaro, A.; Ainis, T.; Fimiani, V. Immunopharmacol. Immunotoxicol. 2003, 25, 441.
15. For studies on the biological properties of lactones containing a 6-substituted 5,6-dihydropyran-2-one moiety, see, for example: (a) Stampwala, S. S.; Bunge, R. H.; Hurley, T. R.; Willmer, N. E.; Brankiewicz, A. J.; Steinman, C.E.; Smitka, T. A.; French, J. C. J. Antibiot. 1983, 36, 1601. (b) Davis, R. M.; Richard, J. L. Dev. Food Sci. 1984, 8, 315. (c) Nagashima, H.; Nakamura, K.; Goto, T. Biochem. Biophys. Res. Commun. 2001, 287, 829. (d) Raoelison, G. E.; Terreaux, C.; Queiroz, E. F.; Zsila, F.; Simonyi, M.; Antus, S.; Randriantsoa, A.; Hostettmann, K. Helv. Chim. Acta 2001, 84, 3470. (e) Kalesse, M.; Christmann, M. Synthesis 2002, 981-1003. (f) Lewy, D. S.; Gauss, C.-M.; Soenen, D. R.; Boger, D. L. Curr. Med. Chem. 2002, 9, 2005. (g) Larsen, A. K.; Escargueil, A. E.; Skladanowski, A. Pharmacol. Ther. 2003, 99, 167-181. (h) Richetti, A.; Cavallaro, A.; Ainis, T.; Fimiani, V. Immunopharmacol. Immunotoxicol. 2003, 25, 441.
16. For studies on the biological properties of lactones containing a 6-substituted 5,6-dihydropyran-2-one moiety, see, for example: (a) Stampwala, S. S.; Bunge, R. H.; Hurley, T. R.; Willmer, N. E.; Brankiewicz, A. J.; Steinman, C.E.; Smitka, T. A.; French, J. C. J. Antibiot. 1983, 36, 1601. (b) Davis, R. M.; Richard, J. L. Dev. Food Sci. 1984, 8, 315. (c) Nagashima, H.; Nakamura, K.; Goto, T. Biochem. Biophys. Res. Commun. 2001, 287, 829. (d) Raoelison, G. E.; Terreaux, C.; Queiroz, E. F.; Zsila, F.; Simonyi, M.; Antus, S.; Randriantsoa, A.; Hostettmann, K. Helv. Chim. Acta 2001, 84, 3470. (e) Kalesse, M.; Christmann, M. Synthesis 2002, 981-1003. (f) Lewy, D. S.; Gauss, C.-M.; Soenen, D. R.; Boger, D. L. Curr. Med. Chem. 2002, 9, 2005. (g) Larsen, A. K.; Escargueil, A. E.; Skladanowski, A. Pharmacol. Ther. 2003, 99, 167-181. (h) Richetti, A.; Cavallaro, A.; Ainis, T.; Fimiani, V. Immunopharmacol. Immunotoxicol. 2003, 25, 441.
17. Lichtenthaler, F.; Lorenz, K.; Ma, W. Tetrahedron Lett. 1987, 28, 47.
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19. (c) Valverde, S.; Hernández, A.; Herradón, B.; Rabanal, R. M.; Martín-Lomas, M. Tetrahedron 1987, 43, 3499.
20. Falomir, E.; Murga, J.; Ruiz, P.; Carda, M.; Marco, J.A.; Pereda-Miranda, R.; Fragoso-Serrano, M.; Cerda-García-Rojas, C. M. J. Org. Chem. 2003, 68, 5672.
21. (b) Díaz-Oltra, S.; Murga, J.; Falomir, E.; Carda, M.; Marco, J. A. Tetrahedron 2004, 60, 2979.
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23. Collett, L. A.; Davies-Coleman, M. T.; Rivett, D. E. A. Phytochemistry 1998, 48, 651.
24. For other syntheses of our group, where a related concept was used, see: (a) Carda, M.; Rodríguez, S.; Segovia, B.; Marco, J. A. J. Org. Chem. 2002, 67, 6560. (b) Carda, M.; Rodríguez, S.; Castillo, E.; Bellido, A.; Díaz-Oltra, S.; Marco, J. A. Tetrahedron 2003, 59, 857. (c) García-Fortanet, J.; Murga, J.; Carda, M.; Marco, J. A. Org. Lett. 2003, 5, 1447. (d) Murga, J.; García-Fortanet, J.; Carda, M.; Marco, J. A. J. Org. Chem. 2004, 69, 7277.
25. For other syntheses of our group, where a related concept was used, see: (a) Carda, M.; Rodríguez, S.; Segovia, B.; Marco, J. A. J. Org. Chem. 2002, 67, 6560. (b) Carda, M.; Rodríguez, S.; Castillo, E.; Bellido, A.; Díaz-Oltra, S.; Marco, J. A. Tetrahedron 2003, 59, 857. (c) García-Fortanet, J.; Murga, J.; Carda, M.; Marco, J. A. Org. Lett. 2003, 5, 1447. (d) Murga, J.; García-Fortanet, J.; Carda, M.; Marco, J. A. J. Org. Chem. 2004, 69, 7277.
26. For other syntheses of our group, where a related concept was used, see: (a) Carda, M.; Rodríguez, S.; Segovia, B.; Marco, J. A. J. Org. Chem. 2002, 67, 6560. (b) Carda, M.; Rodríguez, S.; Castillo, E.; Bellido, A.; Díaz-Oltra, S.; Marco, J. A. Tetrahedron 2003, 59, 857. (c) García-Fortanet, J.; Murga, J.; Carda, M.; Marco, J. A. Org. Lett. 2003, 5, 1447. (d) Murga, J.; García-Fortanet, J.; Carda, M.; Marco, J. A. J. Org. Chem. 2004, 69, 7277.
27. For other syntheses of our group, where a related concept was used, see: (a) Carda, M.; Rodríguez, S.; Segovia, B.; Marco, J. A. J. Org. Chem. 2002, 67, 6560. (b) Carda, M.; Rodríguez, S.; Castillo, E.; Bellido, A.; Díaz-Oltra, S.; Marco, J. A. Tetrahedron 2003, 59, 857. (c) García-Fortanet, J.; Murga, J.; Carda, M.; Marco, J. A. Org. Lett. 2003, 5, 1447. (d) Murga, J.; García-Fortanet, J.; Carda, M.; Marco, J. A. J. Org. Chem. 2004, 69, 7277.
28. Fronza, G.; Fuganti, C.; Grasselli, P.; Pedrocchi-Fantoni, G.; Zirotti, C. Tetrahedron Lett. 1982, 23, 4143. For a recent paper on the synthesis of boivinose and other 2,6-dideoxyhexoses, with numerous references to previous work on this topic, see: Ulven, T.; Carlsen, P. H. J. Eur. J. Org. Chem. 2001, 3367.
29. Fronza, G.; Fuganti, C.; Grasselli, P.; Pedrocchi-Fantoni, G.; Zirotti, C. Tetrahedron Lett. 1982, 23, 4143. For a recent paper on the synthesis of boivinose and other 2,6-dideoxyhexoses, with numerous references to previous work on this topic, see: Ulven, T.; Carlsen, P. H. J. Eur. J. Org. Chem. 2001, 3367.
30. Kobayashi, S.; Wakabayashi, T.; Yasuda, M. J. Org. Chem. 1998, 63, 4868. These authors obtained aldehyde 7 by means of a three-step sequence which includes an asymmetric aldol reaction. We have prepared 7 from the known asymmetric dihydroxylation product of ethyl sorbate (Xu, D.; Crispino, G. A.; Sharpless, K. B. J. Am. Chem. Soc. 1992, 114, 7570). For details, see the Experimental Section.
31. Kobayashi, S.; Wakabayashi, T.; Yasuda, M. J. Org. Chem. 1998, 63, 4868. These authors obtained aldehyde 7 by means of a three-step sequence which includes an asymmetric aldol reaction. We have prepared 7 from the known asymmetric dihydroxylation product of ethyl sorbate (Xu, D.; Crispino, G. A.; Sharpless, K. B. J. Am. Chem. Soc. 1992, 114, 7570). For details, see the Experimental Section.
32. The chiral allylboranes used in this paper were prepared as described in the literature from allylmagnesium bromide and the appropriate enantiomer of the commercially available diiso-pinocampheylboron chloride. See: Ramachandran, P. V.; Chen, G.-M.; Brown, H. C. Tetrahedron Lett. 1997, 38, 2417. For a recent review on asymmetric allylborations, see: Ramachandran, P. V. Aldrichimica Acta 2002, 35, 23.
33. The chiral allylboranes used in this paper were prepared as described in the literature from allylmagnesium bromide and the appropriate enantiomer of the commercially available diiso-pinocampheylboron chloride. See: Ramachandran, P. V.; Chen, G.-M.; Brown, H. C. Tetrahedron Lett. 1997, 38, 2417. For a recent review on asymmetric allylborations, see: Ramachandran, P. V. Aldrichimica Acta 2002, 35, 23.
34. The relative configuration of the three stereocenters was checked by desilyation of 8 to a known xylo-1,2,3-triol: Roush, W. R.; Brown, R. J. J. Org. Chem. 1983, 48, 5093.
35. Blanchette, M. A.; Choy, W.; Davis, J. T.; Essenfeld, A. P.; Masamune, S.; Roush, W. R.; Sakai, T. Tetrahedron Lett. 1984, 25, 2183.
36. Trnka, T.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18.
37. As with the other pairs of epimers, our efforts to separate these two lactones via HPLC were unsuccessful.
38. No authentic sample of synargentolide A was available to us for a direct comparison. NMR spectra of the natural compound were sent to us by M. T. Davies-Coleman (see Acknowledgments).
39. 13C chemical shift value of the terminal methyl group at about 15 ppm. Lactones 5, 6, and synargentolide A show this signal above 16 ppm. This supports the conclusion that synargentolide A does not have an anti, anti relative configuration in its side chain as has lactone ii. (Chemical Presented)