A symmetry-based approach to zaragozic acid: Synthesis and end- differentiation of an advanced intermediate

Tetrahedron Letters

Volumn 39, Issue 47, 1998, Pages 8567-8570

  Freeman Cook, Kevin D ^a   Halcomb, Randall L ^a  

^a UNIVERSITY OF COLORADO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

FURAN; ZARAGOZIC ACID A;

ARTICLE; DRUG SYNTHESIS; HYDROXYLATION; PHOTOOXIDATION; STEREOCHEMISTRY;

EID: 0032547970     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01959-5     Document Type: Article

References (33)

1. 1. Howard Hughes Medical Institute Predoctoral Fellow
2. 2. (a) Bergstrom, J. D.; et al. Proc. Natl. Acad. Sci. USA 1993, 90, 80.
3. (b) Baxter, A.; Fitzgerald, B. J.; Hutson, J. L.; McCarthy, A. D.; Motteram, J. M.; Ross, B. C.; Sapra, M.; Snowden, M. A.; Watson, N. S.; Williams, R. J.; Wright, C. J. Biol. Chem. 1992, 267, 11705.
4. 3. Tamonoi, F. Trends Biochem. Sci. 1993, 18, 349.
5. 4. Freeman-Cook, K. D.; Halcomb, R. L. Tetrahedron Letters 1996, 37, 4883.
6. 5. For a review, see: Nadin, A.; Nicolaou, K. C. Angew. Chem. Int. Ed. Engl. 1996, 35, 1623.
7. 6. Total syntheses of zaragozic acid: (a) Carreira, E. M.; Du Bois, J. J. Am. Chem. Soc. 1995, 117, 8106.
8. (b) Nicolaou, K. C.; Yue, E. W.; La Greca, S.; Nadin, A.; Yang, Z.; Leresche, J. E.; Tsuri, T.; Naniwa, Y.; De Riccardis, F. Chem. Eur. J. 1995, 1, 467.
9. (c) Evans, D. A.; Barrow, J. C.; Leighton, J. L.; Robichaud, A. J.; Sefkow, M. J. Am. Chem. Soc. 1994, 116, 12111.
10. (d) Stoermer, D.; Caron, S.; Heathcock, C. H. J. Org. Chem. 1996, 61, 9115.
11. (e) Caron, S.; Stoermer, D.; Mapp, K. A.; Heathcock, C. H. J. Org. Chem. 1996, 61, 9126.
12. (f) Sato, H.; Nakamura, S.-i.; Watanabe, N.; Hashimoto, S.-i. Synlett 1997, 451.
13. (g) Armstrong, A.; Jones, L. H.; Barsanti, P. A. Tetrahedron Lett. 1998, 39, 3337.
14. 7. Recent synthetic efforts: (a) Kraus, G. A.; Maeda, H. J. Org. Chem. 1995, 60, 2.
15. (b) Hegde, S. G.; Myles, D. C. Tetrahedron 1997, 53, 11179.
16. (c) Xu, Y.; Johnson, C. R. Tetrahedron Lett. 1997, 38, 1117.
17. (d) Paterson, I.; Feßner, K.; Findlay, M. R. V. Tetrahedron Lett. 1997, 38, 4301.
18. (e) Maezaki, N.; Gijsen, H. J. M.; Sun, L.-Q.; Paquette, L. A. J. Org. Chem. 1996, 61, 6685.
19. (f) Brogan, J. B.; Zercher, C. K. Tetrahedron Lett. 1998, 39, 1691.
20. 8. Review of two directional chain synthesis: Poss, C. S.; Schreiber, S. L. Acc. Chem. Res. 1994, 27, 9.
21. 9. (a) Cook, M. J.; Forbes, E. J. Tetrahedron 1968, 24, 4501.
22. (b) Lombardo, L.; Sondheimer, F. Synthesis 1980, 11, 950.
23. 10. The assignment of the (S,S) configuration for tetraol 9 is based on empirical NMR correlation of the corresponding bis-Mosher ester (refs. 10a, 11), the Sharpless mnemonic (ref. 10b), and results from related systems (ref. 7h). (a) Dale, J. A.; Mosher, H. S. J. Am. Chem. Soc. 1973, 95, 512.
24. (b) Sharpless, K. B.; Amberg, W.; Bennani, Y.; Crispino, G.; Hartung, J.; Jeong, K.-S.; Kwong, H.-L.; Morikawa, K.; Wang, Z.-M.; Xu, D.; Zhang, X. L. J. Org. Chem. 1992, 57, 2768.
25. 1H NMR spectroscopy was used to measure the diastereomeric ratio of the bis-Mosher esters (Ward, D. E.; Rhee, C. K. Tetrahedron Lett. 1991, 32, 7165). The >100:1 ratio of diastereomers (corresponding to >98% ee) probably is a minimum value, and beyond the limit of accuracy that can be expected by this method. Additional support for this determination was provided by measuring the ratio of diastereomers produced in the dihydroxylation. An ee of 97.6% was calculated by this method. For a mathematical description of related ee enhancements: Schreiber, S. L.; Schreiber, T. S., Smith, D. B. J. Am. Chem. Soc. 1987, 109, 1525.
26. 1H NMR spectroscopy was used to measure the diastereomeric ratio of the bis-Mosher esters (Ward, D. E.; Rhee, C. K. Tetrahedron Lett. 1991, 32, 7165). The >100:1 ratio of diastereomers (corresponding to >98% ee) probably is a minimum value, and beyond the limit of accuracy that can be expected by this method. Additional support for this determination was provided by measuring the ratio of diastereomers produced in the dihydroxylation. An ee of 97.6% was calculated by this method. For a mathematical description of related ee enhancements: Schreiber, S. L.; Schreiber, T. S., Smith, D. B. J. Am. Chem. Soc. 1987, 109, 1525.
27. 12. Ichikawa, Y.; Tsuboi, K.; Naganawa, A.; Isobe, M. Synlett 1993, 12, 907.
28. 13. The details of the X-ray crystallography will be published in a forthcoming full account of this work.
29. 14. Weitz, D. J.; Bednarski, M. D. J. Org. Chem. 1989, 54, 4957.
30. 15. Balkrishna, S. B.; Childers, W. E.; Pinnick, H. W. Tetrahedron Lett. 1981, 37, 2091.
31. 16. Mathias, L. J. Synthesis 1979, 8, 561.
32. 17. The similarity of 19 to an intermediate in Nicolaou's synthesis of zaragozic acid (ref. 6b) is noted.
33. +: 481.1894, found: 481.1865. X-ray crystal structure of 16: (Equation Presented)