New Approach to Bicyclo[5.3.0]decanes: Stereoselective Guaiane Synthesis

Organic Letters

Volumn 5, Issue 23, 2003, Pages 4453-4455

  Coquerel, Yoann ^a   Greene, Andrew E ^a   Deprés, Jean Pierre ^a  

^a UNIVERSITÉ JOSEPH FOURIER   (France)

Author keywords

[No Author keywords available]

Indexed keywords

GUAIAN 8,12 OLIDE 6 DEOXYGEIGERIN; SESQUITERPENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CYCLOADDITION; METHODOLOGY; STEREOCHEMISTRY; SYNTHESIS;

EID: 0344496736     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol035763g     Document Type: Article

References (32)

1. See: Dictionary of Terpenoids; Connolly, J. D.; Hill, R. A., Eds.; Chapman and Hall: New York, 1991. See also: Hanson, J. R. Nat. Prod. Rep. 2002,19, 125-132. Fraga, B. M. Nat. Prod. Rep. 2002, 19, 650-672 and references therein.
2. See: Dictionary of Terpenoids; Connolly, J. D.; Hill, R. A., Eds.; Chapman and Hall: New York, 1991. See also: Hanson, J. R. Nat. Prod. Rep. 2002,19, 125-132. Fraga, B. M. Nat. Prod. Rep. 2002, 19, 650-672 and references therein.
3. See: Dictionary of Terpenoids; Connolly, J. D.; Hill, R. A., Eds.; Chapman and Hall: New York, 1991. See also: Hanson, J. R. Nat. Prod. Rep. 2002,19, 125-132. Fraga, B. M. Nat. Prod. Rep. 2002, 19, 650-672 and references therein.
4. See: Heathcock, C. H.; Graham, S. L.; Pirrung, M. C.; Plavac, F.; White, C. T. In The Total Synthesis of Natural Products; ApSimon, J., Ed.; Wiley-Interscience: New York, 1983; Vol. 5. For some recent examples, see: Lee, K.; Cha, J. K. J. Am. Chem. Soc. 2001, 123, 5590-5591. Trost, B. M.; Shen, H. C. Angew. Chem., Int. Ed. 2001, 40, 2313-2316. Lin, S.; Dudley, G. B.; Tan, D. S. ; Danishefsky, S. J. Angew. Chem., Int. Ed. 2002, 41, 2188-2191. Kumar, J. S. R.; O'Sullivan, M. F.; Reisman, S. E.; Hulford, C. A.; Ovaska, T. V. Tetrahedron Lett. 2002, 43, 1939-1941. Winkler, J. D.; Rouse, M. B.; Greaney, M. F.; Harrison, S. J.; Jeon, Y. T. J. Am. Chem. Soc. 2002, 124, 9726-9728, and references therein.
5. See: Heathcock, C. H.; Graham, S. L.; Pirrung, M. C.; Plavac, F.; White, C. T. In The Total Synthesis of Natural Products; ApSimon, J., Ed.; Wiley-Interscience: New York, 1983; Vol. 5. For some recent examples, see: Lee, K.; Cha, J. K. J. Am. Chem. Soc. 2001, 123, 5590-5591. Trost, B. M.; Shen, H. C. Angew. Chem., Int. Ed. 2001, 40, 2313-2316. Lin, S.; Dudley, G. B.; Tan, D. S. ; Danishefsky, S. J. Angew. Chem., Int. Ed. 2002, 41, 2188-2191. Kumar, J. S. R.; O'Sullivan, M. F.; Reisman, S. E.; Hulford, C. A.; Ovaska, T. V. Tetrahedron Lett. 2002, 43, 1939-1941. Winkler, J. D.; Rouse, M. B.; Greaney, M. F.; Harrison, S. J.; Jeon, Y. T. J. Am. Chem. Soc. 2002, 124, 9726-9728, and references therein.
6. See: Heathcock, C. H.; Graham, S. L.; Pirrung, M. C.; Plavac, F.; White, C. T. In The Total Synthesis of Natural Products; ApSimon, J., Ed.; Wiley-Interscience: New York, 1983; Vol. 5. For some recent examples, see: Lee, K.; Cha, J. K. J. Am. Chem. Soc. 2001, 123, 5590-5591. Trost, B. M.; Shen, H. C. Angew. Chem., Int. Ed. 2001, 40, 2313-2316. Lin, S.; Dudley, G. B.; Tan, D. S. ; Danishefsky, S. J. Angew. Chem., Int. Ed. 2002, 41, 2188-2191. Kumar, J. S. R.; O'Sullivan, M. F.; Reisman, S. E.; Hulford, C. A.; Ovaska, T. V. Tetrahedron Lett. 2002, 43, 1939-1941. Winkler, J. D.; Rouse, M. B.; Greaney, M. F.; Harrison, S. J.; Jeon, Y. T. J. Am. Chem. Soc. 2002, 124, 9726-9728, and references therein.
7. See: Heathcock, C. H.; Graham, S. L.; Pirrung, M. C.; Plavac, F.; White, C. T. In The Total Synthesis of Natural Products; ApSimon, J., Ed.; Wiley-Interscience: New York, 1983; Vol. 5. For some recent examples, see: Lee, K.; Cha, J. K. J. Am. Chem. Soc. 2001, 123, 5590-5591. Trost, B. M.; Shen, H. C. Angew. Chem., Int. Ed. 2001, 40, 2313-2316. Lin, S.; Dudley, G. B.; Tan, D. S. ; Danishefsky, S. J. Angew. Chem., Int. Ed. 2002, 41, 2188-2191. Kumar, J. S. R.; O'Sullivan, M. F.; Reisman, S. E.; Hulford, C. A.; Ovaska, T. V. Tetrahedron Lett. 2002, 43, 1939-1941. Winkler, J. D.; Rouse, M. B.; Greaney, M. F.; Harrison, S. J.; Jeon, Y. T. J. Am. Chem. Soc. 2002, 124, 9726-9728, and references therein.
8. See: Heathcock, C. H.; Graham, S. L.; Pirrung, M. C.; Plavac, F.; White, C. T. In The Total Synthesis of Natural Products; ApSimon, J., Ed.; Wiley-Interscience: New York, 1983; Vol. 5. For some recent examples, see: Lee, K.; Cha, J. K. J. Am. Chem. Soc. 2001, 123, 5590-5591. Trost, B. M.; Shen, H. C. Angew. Chem., Int. Ed. 2001, 40, 2313-2316. Lin, S.; Dudley, G. B.; Tan, D. S. ; Danishefsky, S. J. Angew. Chem., Int. Ed. 2002, 41, 2188-2191. Kumar, J. S. R.; O'Sullivan, M. F.; Reisman, S. E.; Hulford, C. A.; Ovaska, T. V. Tetrahedron Lett. 2002, 43, 1939-1941. Winkler, J. D.; Rouse, M. B.; Greaney, M. F.; Harrison, S. J.; Jeon, Y. T. J. Am. Chem. Soc. 2002, 124, 9726-9728, and references therein.
9. See: Heathcock, C. H.; Graham, S. L.; Pirrung, M. C.; Plavac, F.; White, C. T. In The Total Synthesis of Natural Products; ApSimon, J., Ed.; Wiley-Interscience: New York, 1983; Vol. 5. For some recent examples, see: Lee, K.; Cha, J. K. J. Am. Chem. Soc. 2001, 123, 5590-5591. Trost, B. M.; Shen, H. C. Angew. Chem., Int. Ed. 2001, 40, 2313-2316. Lin, S.; Dudley, G. B.; Tan, D. S. ; Danishefsky, S. J. Angew. Chem., Int. Ed. 2002, 41, 2188-2191. Kumar, J. S. R.; O'Sullivan, M. F.; Reisman, S. E.; Hulford, C. A.; Ovaska, T. V. Tetrahedron Lett. 2002, 43, 1939-1941. Winkler, J. D.; Rouse, M. B.; Greaney, M. F.; Harrison, S. J.; Jeon, Y. T. J. Am. Chem. Soc. 2002, 124, 9726-9728, and references therein.
10. Günther, H.; Görlitz, M.; Hinrichs, H. H. Tetrahedron 1968, 24, 5665-5676. Tropylium tetrafluoroborate is now commercially available.
11. Coquerel, Y.; Blanc, A.; Deprés, J.-P.; Greene, A. E.; Averbuch-Pouchot, M.-T.; Philouze, C.; Durif, A. Acta Crystallogr. 2000, C56, 1480-1481. For an application, see: Yokoyama, R.; Ito, S.; Watanabe, M.; Harada, N.; Kabuto, C.; Morita, N. J. Chem. Soc., Perkin Trans. 1 2001, 2257-2261.
12. Coquerel, Y.; Blanc, A.; Deprés, J.-P.; Greene, A. E.; Averbuch-Pouchot, M.-T.; Philouze, C.; Durif, A. Acta Crystallogr. 2000, C56, 1480-1481. For an application, see: Yokoyama, R.; Ito, S.; Watanabe, M.; Harada, N.; Kabuto, C.; Morita, N. J. Chem. Soc., Perkin Trans. 1 2001, 2257-2261.
13. (a) Greene, A. E.; Deprés, J.-P. J. Am. Chem. Soc. 1979, 101, 4003-4005.
14. (b) Deprés, J.-P.; Greene, A. E. J. Org. Chem. 1980, 45, 2036-2037.
15. Marshall, J. A.; Partridge, J. J. J. Org. Chem. 1968, 33, 4090-4097. The use of diazoethane with the cycloheptatriene cycloadduct leads stereoselectively to the β-methyl trienone derivative (NOE).
16. Structure and stereochemistry of 5b, 6, and 9b were determined by X-ray diffraction analysis. Crystallographic information files (CIF) for 5b, 6, and 9b have been deposited at the Cambridge Crystallographic Data Centre and can be obtained online free of charge (or upon request from the Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB2 1EZ, UK. Fax: (+44) 1223-336-033. E-mail: deposit@ccdc.cam.ac.uk).
17. For leading references on recent applications of iron carbonyls in synthesis, see: Coquerel, Y. Synlett 2002, 1937-1938.
18. Wilcox, C. S.; Babston, R. E. J. Org. Chem. 1984, 49, 1451-1453. Reetz, M. T.; Fox, D. N. A. Tetrahedron Lett. 1993, 34, 1119-1122.
19. Wilcox, C. S.; Babston, R. E. J. Org. Chem. 1984, 49, 1451-1453. Reetz, M. T.; Fox, D. N. A. Tetrahedron Lett. 1993, 34, 1119-1122.
20. Chemical shifts of H6 and H7 are 6.84 and 6.41 ppm, respectively. Similar high-field H8,H9 chemical shifts and parallel regioselectivity were observed with analogues of 3.
21. B3LYP/6-31G* calculation of the coefficients of the frontier orbitals of 3 gives, respectively, for C7 and C9: LUMO 0.29 and 0.25, HOMO 0.20 and 0.22. The partial nonconjugated character of the C8,C9 double bond is also suggested by the calculated C6,C7-C8,C9 dihedral angle (15.2 vs 2.3° for C4,C5-C6,C7).
22. Guaciaro, M. A.; Wovkulich, P. M.; Smith, A. B., III. Tetrahedron Lett. 1978, 4661-4664. Bachki, A.; Foubelo, F.; Yus, M. Tetrahedron 1997, 53, 4921-4934.
23. Guaciaro, M. A.; Wovkulich, P. M.; Smith, A. B., III. Tetrahedron Lett. 1978, 4661-4664. Bachki, A.; Foubelo, F.; Yus, M. Tetrahedron 1997, 53, 4921-4934.
24. (a) Ishii, H.; Tozyo, T.; Nakamura, M.; Minato, H. Tetrahedron 1970, 26, 2751-2757.
25. (b) From natural sources: Jakupovic, J.; Pathak, V. P.; Grenz, M.; Banerjee, S.; Wolfrum, C.; Baruah, R. N.; Bohlmann, F. Phytochemistry 1987, 26, 1049-1052. Handayani, D.; Edrada, R. A.; Proksch, P.; Wray, V.; Witte, L.; van Ofwegen, L.; Kunzmann, A. J. Nat. Prod. 1997, 60, 716-718. Labbé, C.; Faini, F.; Coll, J.; Carbonell, P. Phytochemistry 1998, 49, 793-795.
26. (b) From natural sources: Jakupovic, J.; Pathak, V. P.; Grenz, M.; Banerjee, S.; Wolfrum, C.; Baruah, R. N.; Bohlmann, F. Phytochemistry 1987, 26, 1049-1052. Handayani, D.; Edrada, R. A.; Proksch, P.; Wray, V.; Witte, L.; van Ofwegen, L.; Kunzmann, A. J. Nat. Prod. 1997, 60, 716-718. Labbé, C.; Faini, F.; Coll, J.; Carbonell, P. Phytochemistry 1998, 49, 793-795.
27. (b) From natural sources: Jakupovic, J.; Pathak, V. P.; Grenz, M.; Banerjee, S.; Wolfrum, C.; Baruah, R. N.; Bohlmann, F. Phytochemistry 1987, 26, 1049-1052. Handayani, D.; Edrada, R. A.; Proksch, P.; Wray, V.; Witte, L.; van Ofwegen, L.; Kunzmann, A. J. Nat. Prod. 1997, 60, 716-718. Labbé, C.; Faini, F.; Coll, J.; Carbonell, P. Phytochemistry 1998, 49, 793-795.
28. Procopiou, P. A.; Baugh, S. P. D.; Flack, S. S.; Inglis, G. G. A. J. Org. Chem. 1998, 63, 2342-2347.
29. Ryu, J.-H.; Jeong, Y. S. Arch. Pharm. Res. 2001, 24, 532-535.
30. Zdero, C.; Bohlmann, F. Phytochemistry 1989, 28, 3105-3120.
31. Barton, D. H. R.; Pinhey, J. T.; Wells, R. J. J. Chem. Soc. 1964, 2518-2526.
32. 3 to give an advanced pseudoguaianolide precursor.