The use of vinyl sulfonium salts in the stereo-controlled asymmetric synthesis of epoxide- and aziridine-fused heterocycles: Application to the synthesis of (-)-balanol

Angewandte Chemie - International Edition

Volumn 45, Issue 42, 2006, Pages 7066-7069

  Unthank, Matthew G ^a   Hussain, Nigel ^b   Aggarwal, Varinder K ^a  

^a UNIVERSITY OF BRISTOL   (United Kingdom)

^b GLAXOSMITHKLINE   (United Kingdom)

Author keywords

Annulation; Asymmetric synthesis; Natural products; Ring opening; Sulfur ylides

Indexed keywords

ALCOHOLS; KETONES; SULFUR COMPOUNDS; SYNTHESIS (CHEMICAL);

ANNULATION; ASYMMETRIC SYNTHESIS; HETEROCYCLIC EPOXIDES; NATURAL PRODUCTS; RING OPENING; VINYL SULFONIUM SALTS;

SALTS;

EID: 33750630993     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200602782     Document Type: Article

References (36)

1. a) V. K. Aggarwal, C. L. Winn, Acc. Chem. Res. 2004, 37, 611-620;
2. b) V. K. Aggarwal, J. Richardson, Chem. Commun. 2003, 2644-2651.
3. a) K. Kim, L. S. Jimenez, Tetrahedron: Asymmetry 2001, 12, 999-1005, and references therein;
4. b) Y. Wang, W. Zhang, J. V. Colandrea, L. S. Jimenez, Tetrahedron 1999, 55, 10 659-10 672.
5. a) P. Kulanthaivel, Y. F. Hallock, C. Boros, S. M. Hamilton, W. P. Janzen, L. M. Ballas, C. R. Loomis, J. B. Jiang, B. Katz, J. R. Steiner, J. Clardy, J. Am. Chem. Soc. 1993, 115, 6452-6453;
6. b) J. M. Defauw, M. M. Murphy, G. E. Jagdmann, Jr., H. Hu, J. W. Lampe, S. P. Hollinshead, T. J. Mitchell, H. H. Crane, J. M. Heerding, J. S. Mendoza, J. E. Davis, J. W. Darges, F. R. Hubbard, S. E. Hall, J. Med. Chem. 1996, 39, 5215-5227.
7. a) K. A. Tehrani, T. N. Van, M. Karikomi, M. Rottiers, N. De Kimpe, Tetrahedron 2002, 58, 7145-7152;
8. b) S. Liu, R. P. Hanzlik, J. Med. Chem. 1992, 35, 1067-1075.
9. H. Ohno, K. Miyamura, T. Tanaka, S. Oishi, A. Toda, Y. Takemoto, N. Fujii, T. Ibuka, J. Org. Chem. 2002, 67, 1359-1367.
10. a) S. A. Harkin, O. Singh, E. J. Thomas, J. Chem. Soc. Perkin Trans. 1 1984, 1489-1499;
11. b) J. Ahman, P. Somfai, Tetrahedron 1992, 48, 9537-9544.
12. V. K. Aggarwal, E. Alonso, I. Bae, G. Hynd, K. M. Lydon, M. J. Palmer, M. Patel, M. Porcelloni, J. Richardson, R. Stenson, J. R. Studley, J. L. Vasse, C. L. Winn, J. Am. Chem. Soc. 2003, 125, 10 926-10 940.
13. a) V. K. Aggarwal, I. Bae, H.-Y. Lee, D. T. Williams, Angew. Chem. 2003, 115, 3396-3400;
14. Angew. Chem. Int. Ed. 2003, 42, 3274-3278.
15. a) T. R. Kasturi, L. Mathew, J. A. Sattigeri, Indian J. Chem. Sect. B 1990, 29, 1004-1006;
16. b) W. R. McKay, G. R. Proctor, J. Chem. Soc. Perkin Trans. 1 1981, 2435-2442.
17. For reactions of α-aminoketones with vinyl phosphonium salts to give dihydropyrroles, see: a) I. Burley, A. T. Hewson, Tetrahedron Lett. 1994, 35, 7099-7102;
18. b) C. M. Boynton, A. T. Hewson, M. Douglas, J. Chem. Soc. Perkin Trans. 1 2000, 3599-3602.
19. For reactions of β-aminoaldehydes with vinyl phosphonium salts, see: S. Kumarn, D. M. Shaw, D. A. Longbottom, S. V. Ley, Org. Lett. 2005, 7, 4189-4191.
20. P. Y. Chong, S. Z. Janicki, P. A. Petillo, J. Org. Chem. 1998, 63, 8515-8521.
21. CCDC 614698 and CCDC 614700 (3 and 15b) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/ data_request/cif.
22. a) V. K. Aggarwal, E. Alonso, G. Hynd, K. M. Lydon, M. J. Palmer, M. Porcelloni, J. R. Studley, Angew. Chem. 2001, 113, 1479-1482;
23. Angew. Chem. Int. Ed. 2001, 40, 1430-1433;
24. b) V. K. Aggarwal, J. Charmant, L. Dudin, M. Porcelloni, J. Richardson, Proc. Natl. Acad. Sci. USA 2004, 101, 5467-5471.
25. A. B. Reitz, E. Sonveaux, R. P. Rosenkranz, M. S. Verlander, K. L. Melmon, B. B. Hoffman, Y. Akita, N. Castagnoli, M. Goodman, J. Med. Chem. 1985, 28, 634-642.
26. Enolate formation and subsequent elimination results in the formation of N-tosylsulfonamide, which then underwent conjugate addition to the vinyl sulfonium salt. Following a 1,3-proton shift and subsequent ring closure, the tosyl aziridine was obtained in 45 % yield. (Chemical Equation Presented)
27. For recent reviews, see: a) E. N. Jacobsen, M. H. Wu in Comprehensive Asymmetric Catalysis, Vol. 2 (Eds.: E. N. Jacobsen, A. Pfaltz, H. Yamamoto), Springer, Berlin, 1999, pp. 649-677;
28. b) T. Katsuki in Comprehensive Organic Catalysis, Vol. 2 (Eds.: E. N. Jacobsen, A. Pfaltz, H. Yamamoto), Springer, Berlin, 1999, pp. 621-648.
29. a) P. G. M. Wuts, R. L. Gu, J. M. Northuis, T. A. Kwan, D. M. Beck, M. J. White, Pure Appl. Chem. 2002, 74, 1359-1368;
30. b) T. Katsuki, Adv. Synth. Catal. 2002, 344, 131-147.
31. Y. Shi, Acc. Chem. Res. 2004, 37, 488-496.
32. a) D. Tanner, A. Almario, T. Hogberg, Tetrahedron 1995, 51, 6061-6070;
33. b) D. Tanner, L. Tedenborg, A. Almario, I. Pettersson, I. Csoregh, N. M. Kelly, P. G. Andersson, T. Hogberg, Tetrahedron 1997, 53, 4857-4868.
34. J. A. Ellman, T. D. Owen, T. P. Tang, Acc. Chem. Res. 2002, 35, 984-995.
35. Attempts to improve the diastereoselectivity through the reaction of aminal 14 with the chiral vinyl sulfonium salt 6 did not result in the formation of the desired aziridine 15. Enolization α to the imine 14 and subsequent conjugate addition of the enolate to the chiral vinyl sulfonium salt 6 gave an ylide, which underwent 1,3-proton shift and ring closure to form the α-cyclopropylimine 18. (Chemical Equation Presented)
36. For the shortest previously reported route to balanol (ten linear steps), see: a) A. Fürstner, O. R. Thiel, J. Org. Chem. 2000, 65, 1738-1742; Leading references to other total syntheses of balanol are contained therein.