Stereoselective Total Synthesis of (+)-Norrisolide

Angewandte Chemie - International Edition

Volumn 43, Issue 6, 2004, Pages 739-742

  Brady, Thomas P ^a   Kim, Sun Hee ^a   Wen, Ke ^a   Theodorakis, Emmanuel A ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

Alkylation; Diels Alder reaction; Natural products; Synthetic methods; Total synthesis

Indexed keywords

OXIDATION; SYNTHESIS (CHEMICAL);

BICYCLIC RING SYSTEMS;

ORGANIC COMPOUNDS;

CARBON; GAMMA LACTONE DERIVATIVE; NATURAL PRODUCT; NORRISOLIDE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL BOND; CHEMICAL STRUCTURE; NONHUMAN; OXIDATION; STEREOCHEMISTRY; SYNTHESIS;

ANIMALS; CRYSTALLOGRAPHY, X-RAY; DITERPENES; MODELS, CHEMICAL; MOLECULAR STRUCTURE; MOLLUSCA; STEREOISOMERISM;

EID: 1042279650     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200352868     Document Type: Article

References (45)

1. For selected reviews, see: a) D. J. Faulkner in Biomedical Importance of Marine Organisms, Vol. 13 (Ed.: D. G. Fautin), Memoirs California Academy of Sciences, San Francisco, CA, 1988, pp. 29-36;
2. b) P. Karuso in Bioorganic Marine Chemistry (Ed.: P. J. Scheuer), Springer, Berlin, 1987, pp 31-60;
3. c) D. J. Faulkner, Nat. Prod. Rep. 1984, 1, 251-280;
4. d) T. E. Thompson, J. Mar. Biol. Assoc. U. K. 1960, 39, 115-122.
5. For selected natural products isolated from nudibranchs, see: a) B. J. Burreson, P. J. Scheuer, J. Finer, J. Clardy, J. Am. Chem. Soc. 1975, 97, 4763-4764;
6. b) E. J. Dumbei, E. D. de Silva, R. J. Andersen, M. I. Choudhary, J. Clardy, J. Am. Chem. Soc. 1989, 111, 2712-2713;
7. c) B. Carte, D. J. Faulkner, J. Chem. Ecol. 1986, 12, 795-804;
8. d) G. Cimino, S. De Rosa, S. De Stefano, G. Sodano, G. Villani, Science 1983, 219, 1237-1238;
9. e) M. Tischler, R. J. Andersen, Tetrahedron Lett. 1989, 30, 5717-5720.
10. J. E. Hochlowski, D. J. Faulkner, G. K. Matsumoto, J. Clardy, J. Org. Chem. 1983, 48, 1141-1142.
11. a) B. Sullivan, D. J. Faulkner, J. Org. Chem. 1984, 49, 3204-3206;
12. b) A. Rudi, Y. Kashman, Tetrahedron 1990, 46, 4019-4022.
13. a) S. C. Bobzin, D. J. Faulkner, J. Org. Chem. 1989, 54, 5727-5731;
14. b) T. F. Molinski, D. J. Faulkner, J. Org. Chem. 1986, 51, 4564-4567.
15. For recent biological data on related metabolites, see: M. Arno, L. Betancur-Galvis, M. A. Gonzalez, J. Sierra, R. J. Zaragoza, Bioorg. Med. Chem. 2003, 11, 3171-3177.
16. For synthetic studies toward 1, see: a) C. Kim, R. Hoang, E. A. Theodorakis, Org. Lett. 1999, 1, 1295-1297;
17. b) R. L. Casaubon, M. L. Snapper, 224th ACS Natl. Meeting, Boston, USA, 2002.
18. For selected syntheses of related metabolites, see: a) A. D. Lebsack, L. E. Overman, R. J. Valentekovich, J. Am. Chem. Soc. 2001, 123, 4851-4852;
19. b) A. Abad, M. Arno, M. L. Marin, R. J. Zaragoza, J. Org. Chem. 1992, 57, 6861-6864;
20. c) M. Arno, M. A. Gonzalez, R. J. Zaragoza, J. Org. Chem. 2003, 68, 1242-1251.
21. For a catalytic asymmetric Diels-Alder approach to a related tricyclic γ-lactone-γ-lactol ring system, see: E. J. Corey, M. A. Letavic, J. Am. Chem. Soc. 1995, 117, 9616-9617.
22. For selected reports on the Baeyer-Villiger reaction, see: a) M. Hudlicky in Oxidations in Organic Chemistry, American Chemical Society, Washington, DC, 1990, pp. 186-195;
23. b) K. Mislow, J. Brenner, J. Am. Chem. Soc. 1953, 75, 2318-2322;
24. c) R. M. Goodman, Y. Kishi, J. Am. Chem. Soc. 1998, 120, 9392-9393.
25. a) U. Eder, G. Sauer, R. Wiechert, 1971, 83, 492-493;
26. b) Z. G. Hajos, D. R. Parrish, (Hoffmann-La Roche, Inc.), US 70-96597, 1976 [Chem. Abstr. 1977, 86, 89274];
27. c) H. Hagiwara, J. Uda, J. Org. Chem. 1988, 53, 2308-2311;
28. d) H. Hagiwara, H. Sakai, T. Uchiyama, Y. Ito, N. Morita, T. Hoshi, T. Suzuki, M. Ando, J. Chem. Soc. Perkin Trans. 1 2002, 583-591.
29. All new compounds exhibited satisfactory spectroscopic and analytical data (see Supporting Information). Yields refer to spectroscopically and chromatographically homogeneous materials.
30. All hydrogenation conditions produced a mixture of cis (major product) and trans bicycles, which were difficult to separate by using standard chromatographic techniques.
31. For an alternative synthetic route to 13, see: a) L. Paquette, H.-L. Wang, Tetrahedron Lett. 1995, 36, 6005-6008;
32. b) L. Paquette, H.-L. Wang, J. Org. Chem. 1996, 61, 5352-5357.
33. CCDC-216393 (14) and CCDC-216394 (6) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/conts/retrieving.html (or from the Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB21EZ, UK; fax: (+44)1223-336-033; or deposit@ccdc.cam.ac.uk).
34. a) D. H. R. Barton, R. E. O'Brien, S. Sternhill, J. Chem. Soc. Perkin Trans. 1 1962, 470-476.
35. b) A. Fernandez-Mateos, G. P. Coca, R. R. Gonzalez, C. T. Hernandez, Tetrahedron 1996, 52, 4817-4828.
36. Compound 15 is readily available from D-mannitol by the procedures reported in the following publications: a) C. R. Schmid, J. D. Bryant, M. Dowlatzedah, J. L. Phillips, D. E. Prather, R. D. Shantz, N. L. Sear, C. S. Vianco, J. Org. Chem. 1991, 56, 4056-4058;
37. b) J. Mann, A. Weymouth-Wilson, Carbohydr. Res. 1991, 216, 511-515;
38. c) F. Fazio, M. P. Scheider, Tetrahedron: Asymmetry 2000, 11, 1869-1876.
39. M. G. B. Drew, J. Mann, A. Thomas, J. Chem. Soc. Perkin Trans. 1 1986, 2279-2285.
40. In principle, both C14 isomers can be used for the synthesis of 1. Nonetheless, to facilitate the spectroscopic characterization of the synthetic intermediates the strategy was evaluated with the β isomer (with respect to the substituent at C14).
41. F. Petit, R. Furstoss, Synthesis 1995, 1517-1520.
42. P. J. Kocienski, P. Raubo, C. Smith, F. T. Boyle, Synthesis 1999, 2087-2095.
43. E. J. Corey, M. Ohno, R. B. Mitra, P. A. Vatakencherry, J. Am. Chem. Soc. 1964, 86, 478-485.
44. J. D. Moore, N. S. Finney, Org. Lett. 2002, 4, 3001-3003.
45. Y. Lin, Y. Kuo, Y. Chen, Chem. Pharm. Bull. 1989, 37, 2191-2193.