A symmetry-based approach to the heterobicyclic core of the zaragozic acids - Model studies in the pseudo C2-symmetric series

Advanced Synthesis and Catalysis

Volumn 349, Issue 14-15, 2007, Pages 2361-2367

  Yuzhou, Wang ^a   Gang, Sylvia ^a   Bierstedt, Anja ^a   Gruner, Margit ^a   Fröhlich, Roland ^b   Metz, Peter ^a  

^a DRESDEN UNIVERSITY OF TECHNOLOGY   (Germany)

^b UNIVERSITY OF MÜNSTER   (Germany)

Author keywords

Asymmetric catalysis; Chemoselectivity; Cyclization; Dihydroxylation; Heterocycles; Zaragozic acids

Indexed keywords

EID: 35948936769     PISSN: 16154150     EISSN: 15213897     Source Type: Journal    
DOI: 10.1002/adsc.200700122     Document Type: Article

References (51)

1. For reviews on the synthesis and biological activity of the zaragozic acids/squalestatins, see : a) S. Nakamura, Chem. Pharm. Bull. 2005, 53, 1-10;
2. b) A. Armstrong, T.J. Blench, Tetrahedron 2002, 58, 9321-9349;
3. c) N. Jotterand, P. Vogel, Curr. Org. Chem. 2001, 5, 637-661;
4. d) A. Nadin, K. C. Nicolaou, Angew. Chem. 1996, 108, 1732-1766;
5. Angew. Chem. Int. Ed. 1996, 35, 1622-1656;
6. e) U. Koert, Angew. Chem. 1995, 107, 849-855;
7. Angew. Chem. Int. Ed. 1995, 34, 773-778.
8. a) C. Bate, L. Rumbold, A. Williams, J. Neuroinflammation 2007, 4:5 (doi:10.1186/1742-2094-4-5);
9. b) C. Bate, M. Salmona, L. Diomede, A. Williams, J. Biol. Chem. 2004, 279, 14983-14990.
10. For very recent synthetic work in the area, see : a) Y. Hirata, S. Nakamura, N. Watanabe, O. Kataoka, T. Kurosaki, M. Anada, S. Kitagaki, M. Shiro, S. Hashimoto, Chem. Eur. J. 2006, 12, 8898-8925;
11. b) J. O. Bunte, A. N. Cuzzupe, A. M. Daly, M. A. Rizzacasa, Angew. Chem. 2006, 118, 6524-6528;
12. Angew. Chem. Int. Ed. 2006, 45, 6376-6380;
13. c) M. Tsubuki, H. Okita, T. Honda, Heterocycles 2006, 67, 731-748;
14. d) S. Nakamura, H. Sato, Y Hirata, N. Watanabe, S. Hashimoto, Tetrahedron 2005, 61, 11078-11106, and references,. cited therein;
15. e) E. Negishi, Z. Tan, B. Liang, T. Novak, Proc Natl. Acad. Sci. USA 2004,101, 5782-5787.
16. 2-symmetric series, see: A. Bierstedt, J. Roels, J. Zhang, Y. Wang, R. Fröhlich, P. Metz, Tetrahedron Lett. 2003, 44, 7867-7870.
17. For alternative symmetry-based approaches, see: a) K. D. Freeman-Cook, R. L. Halcomb, J. Org. Chem. 2000, 65, 6153-6159;
18. b) D.J. Wardrop, A.I. Velter, R. E. Forslund, Org. Lett. 2001, 3, 2261-2264.
19. [7c]
20. For reviews on two-directional synthesis, see: a) M. E. Maier, S. Reuter, GIT Fachz. Lab. 1997, 41, 1108, 1110-1112;
21. b) S. R. Magnuson, Tetrahedron 1995, 57, 2167-2213;
22. c) C. S. Poss, S. L. Schreiber, Acc Chem. Res. 1994, 27, 9-17;
23. d) M. E. Maier, Nachr. Chem. Tech. Lab. 1993, 41, 314-316, 318, 321-322, 324-325, 328, 330.
24. For recent examples of intramolecular desymmetrization of pseudo C2-symmetric substrates, see: E. A. Voight, C. Rein, S. D. Burke, J. Org. Chem. 2002, 67, 8489-8499.
25. D. H. G. Crout, V. S. B. Gaudet, K. O. Hallinan, J. Chem. Soc, Perkin Trans. 1 1993, 805-812.
26. We prepared meso diethyl tartrate 4 from diethyl maleate in 89% yield according to the dihydroxylation protocol described for dimethyl maleate: T. K. M. Shing, E.K.W. Tam, V. W.-F. Tai, I. H. F. Chung, Q. Jiang, Chem. Eur. J. 1996, 2, 50-57.
27. Thallous ethoxide has been used successfully with diethyl D-tartrate: a) S. V. Taylor, L. D. Vu, T. P. Begley, U. Schörken, S. Grolle, G. A. Sprenger, S. BringerMeyer, H. Sahm, J. Org. Chem. 1998, 63, 2375-2377;
28. b) H. O. Kalinowski, G. Crass, D. Seebach, Chem. Ber. 1981, 114, 477-487.
29. a) M. Jørgensen, E. H. Iversen, A. L. Paulsen, R. Madsen, J. Org. Chem. 2001, 66, 4630-4634;
30. b) J. M. Nuzillard, A. Boumendjel, G. Massiot, Tetrahedron Lett. 1989, 30, 3779-3780;
31. c) S. Saito, S. Hamano, H. Moriyama, K. Okada, T. Moriwake, Tetrahedron Lett. 1988, 29, 1157-1160.
32. For a review, see: R. A. Johnson, K. B. Sharpless, in Catalytic Asymmetric Synthesis, 2nd edn., (Ed.: I. Ojima), Wiley-VCH, New York, 2000, pp 357-398.
33. The bis-Weinreb amide corresponding to 6 with an isopropylidene protection of the diol, as well as the bismethyl ketone analogues with benzyl or isopropylidene blocking of the diol gave rise to tetrahydrofuran derivatives after a single AD reaction, whereas the bismethyl ketone analogue with TBS-protected diol was not converted at all. Details will be disclosed elsewhere.
34. K. Morikawa, K. B. Sharpless, Tetrahedron Lett. 1993, 34, 5575-5578.
35. Crystallographic data (excluding structure factors) for the structure 8 reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC 635640. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB2 IEZ, UK [fax.: (internat.) + 44 1223/336-033; e-mail: deposit@ccdc.cam.ac.uk].
36. E. Keller, SCHAKAL 99, A Computer Program for the Graphic Representation of Molecular and Crystallographic Models, Universität Freiburg, 1999.
37. For a review on meso compounds in stereoselective synthesis, see: R. W. Hoffmann, Angew. Chem. 2003, 115, 1128-1142;
38. Angew. Chem. Int. Ed. 2003, 42, 1096-1109.
39. A. C. M. Barrett, D. Hamprecht, M. Ohkubo, J. Org. Chem. 1997, 62, 9376-9378.
40. L. He, H.-S. Byun, R. Bittman, J. Org. Chem. 2000, 65, 7627-7633.
41. For amplification of ee through double AD reactions, see: H. Takahata, S. Takahashi, S. Kouno, T. Momose, J. Org. Chem. 1998, 63, 2224-2231, and references cited therein.
42. a) For a review, see: M. Mentzel, H. M. R. Hoffmann, J. Prakt. Chem. 1997, 339, 517-524;
43. b) S. Nahm, S. M. Weinreb, Tetrahedron Lett. 1981, 22, 3815-3818.
44. a) D. A. Evans, J. C. Barrow, J. L. Leighton, A. J. Robichaud, M.J. Sefkow, J. Am. Chem. Soc. 1994, 116, 12111-12112;
45. b) A. Armstrong, P.A. Barsanti, L. H. Jones, G. Ahmed, J. Org. Chem. 2000, 65, 7020-7032.
46. Detailed 2D NMR analyses (COSY, HSQC, HMBC, NOESY) confirmed the depicted relative configuration.
47. M. A. Calter, C. Zhu, R. J. Lachicotte, Org. Lett. 2002, 4, 209-212.
48. [21]).
49. K. Mislow, R. E. O'Brien, H. Schaefer, J. Am. Chem. Soc. 1962, 84, 1940-1944.
50. J. M. Williams, R. B. Jobson, N. Yasuda, G. Marchesini, U.-H. Dolling, E. J. J. Grabowski, Tetrahedron Lett. 1995, 36, 5461-5464.
51. Both fractions, which were readily separated by flash chromatography, contained several compounds, the structures of which could not be rigorously elucidated. Presumably, the two fractions represent mixtures of hemi acetals of the intermediate hexahydroxy diketone corresponding to 28.