Total synthesis of (± )-Haliclonacyclamine C

Angewandte Chemie - International Edition

Volumn 49, Issue 9, 2010, Pages 1599-1602

  Smith, Brian J ^a   Sulikowski, Gary A ^a  

^a VANDERBILT UNIVERSITY SCHOOL OF MEDICINE   (United States)

Author keywords

Alkaloids; Macrocycles; Natural products; Ring closing metathesis; Total synthesis

Indexed keywords

ALKYNE METATHESIS; CHEMICAL EQUATIONS; LINEAR SEQUENCE; MACROCYCLES; MACROCYCLICS; MARINE ALKALOIDS; NATURAL PRODUCTS; RING CLOSING METATHESIS; STEREOSELECTIVE HYDROGENATION; TOTAL SYNTHESIS;

ACETYLENE;

SYNTHESIS (CHEMICAL);

ALKALOID; HALICLONACYCLAMINE C; MACROCYCLIC COMPOUND; PIPERIDINE DERIVATIVE;

ARTICLE; CHEMISTRY; CONFORMATION; STEREOISOMERISM; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

ALKALOIDS; CRYSTALLOGRAPHY, X-RAY; MACROCYCLIC COMPOUNDS; MOLECULAR CONFORMATION; PIPERIDINES; STEREOISOMERISM;

EID: 77649084602     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.200905732     Document Type: Article

References (52)

1. a) R. G. S. Berlinck, Top. Heterocycl. Chem. 2007, 10, 211-238;
2. b) R. J. Andersen, R. W. M. Van Soest, F. Kong in Alkaloids: Chemical and Biological Perspectives, Vol.10 (Ed.: S. W. Pelliter), Pergamon, London, 1996, pp. 301-355.
3. a) A. Cutignano, A. Tramice, S. De Caro, G. Villani, G. Cimino, A. Fontana, Angew. Chem. 2003, 115, 2737-2740;
4. Angew. Chem. Int. Ed. 2003, 42, 2633-2636;
5. b) A. Cutignano, G. Cimino, A. Giordano, G. D'Ippolito, A. Fontana, Tetrahedron Lett. 2004, 45, 2627-2629.
6. a) J. D. Winkler, J. M. Axten, J. Am. Chem Soc. 1998, 120, 6425-6426;
7. b) J. M. Humphrey, Y. S. Liao, A. Ali, T. Rein, Y. L. Wong, H. J. Chen, A. K. Courtney, S. F. Martin, J. Am. Chem. Soc 2002, 124, 8584-8592.
8. N. K. Garg, S. Hiebert, L. E. Overman, Angew. Chem. 2006, 118, 2978-2981;
9. Angew. Chem. Int. Ed. 2006, 45, 2912-2915.
10. a) N. Matzanke, R. J. Gregg, S. M. Weinreb, Org. Prep. Proced. Int. 1998, 30, 1-51;
11. b) J. Quirante, L. Paloma, F. Diaba, X. Vila, J. Bonjoch, J. Org. Chem. 2008, 73, 768-771, and the references therein.
12. a) L. Gil, X. Baucherel, M.-T. Martin, C. Marazano, B. C. Das, Tetrahedron Lett. 1995, 36, 6231-6234;
13. b) M. D. SanchezSalvatori, C. Marazano, J. Org. Chem. 2003, 68, 8883-8889;
14. c) J. C. Wypych, T. M. Nguyen, P. Nuhant, M. Benechie, C. Marazano, Angew. Chem. 2008, 120, 5498-5501;
15. Angew. Chem. Int. Ed. 2008, 47, 5418-5421;
16. d) T. Qu, MS Thesis, Texas A&M University, August 2004.
17. a) M. Jaspars, V. Pasupathy, P. Crews, J. Org. Chem. 1994, 59, 3253-3255;
18. b) B. Harrison, S. Talapatra, E. Lobkovsky, J. Clardy, P. Crews, Tetrahedron Lett. 1996, 37, 9151-9154.
19. a) R. D. Charan, M. J. Garson, I. M. Brereton, A. C. Willis, J. N. A. Hooper, Tetrahedron 1996, 52, 9111-9120;
20. b) R. J. Clark, K. L. Field, R. D. Charan, M. J. Garson, I. M. Brereton, A. C. Willis, Tetrahedron 1998, 54, 8811-8826;
21. c) I. W. Mudianta, M. J. Garson, P. V. Berhardt, Aust. J. Chem. 2009, 62, 667-670.
22. a) Y. R. Torres, R. G. S. Berlinck, A. Magalhes, A. B. Schefer, A. G. Ferreira, E. Hajdu, G. Muricy, J. Nat. Prod. 2000, 63, 1098 -1105;
23. b) J. de Oliveira, A. M. Nascimento, M. H. Kossuga, B. C. Cavalcanti, C. O. Pessoa, M. O. Moraes, M. L. Macedo, A. G. Ferreira, E. Hajdu, U. S. Pinheiro, R. G. S. Berlinck, J. Nat. Prod. 2007, 70, 538-543.
24. For examples of stereocontrol by employing the peripheral functionalization of medium and large rings, see: a) W. C. Still, J. Am. Chem. Soc. 1979, 101, 2493-2495;
25. b) E. Vedejs, V. Gapinski, J. Am. Chem. Soc. 1983, 105, 5058-5061;
26. c) S. L. Schreiber, T. Sammakia, B. Hulin, G. Schulte, J. Am. Chem. Soc. 1986, 108, 2106-2108;
27. d) E. Vedejs, W. H. Dent, D. M. Gapinski, C. K. McClure, J. Am. Chem. Soc. 1987, 109, 5437-5438;
28. e) J. Mulzer, H. M. Kirstein, J. Buschmann, C. Lehmann, P. Luger, J. Am. Chem. Soc. 1991, 113, 910-923;
29. f) E. G. Neeland, J. P. Ounsworth, R. Sims, L. Weiler, J. Am. Chem. Soc. 1994, 116, 7383-7394.
30. a) A. Fürstner, G. Seidel, Angew. Chem. 1998, 110, 1758-1760;
31. Angew. Chem. Int. Ed. 1998, 37, 1734-1736;
32. b) For a review, see: K. C. Nicolaou, P. G. Bulger, D. Sarlah, Angew. Chem. 2005, 117, 4564-4601;
33. Angew. Chem. Int. Ed. 2005, 44, 4490-4527.
34. H. E. Schoemaker, J. Dukink, W. N. Speckamp, Tetrahedron 1978, 34, 163-172.
35. K. Kiewel, Z. S. Luo, G. A. Sulikowski, Org. Lett. 2005, 7, 5163-5165.
36. A four-step preparation of 13 starting from 5-hexen-1-ol is provided in the Supporting Information.
37. a) D. L. Comins, A. Dehghani, Tetrahedron Lett. 1992, 33, 6299-6302;
38. b) W. J. Scott, J. K. Stille, J. Am. Chem. Soc. 1986, 108, 3033-3040;
39. c) W. D. Wulff, G. A. Peterson, W. E. Bauta, K.-S. Chan, K. L. Faron, S. R. Gilbertson, R. W. Kaesler, D. C. Yang, C. K. Murray, J. Org. Chem. 1986, 51, 277-279.
40. X. Han, B. M. Stoltz, E. J. Corey, J. Am. Chem. Soc. 1999, 121, 7600-7605.
41. L. Del Valle, J. K. Stille, L. S. Hegedus, J. Org. Chem. 1990, 55, 3019-3023.
42. For reviews, see: a) R. H. Grubbs, S. J. Miller, G. C. Fu, Acc. Chem. Res. 1995, 28, 446-452;
43. b) R. H. Grubbs, S. Chang, Tetrahedron 1998, 54, 4413-4450;
44. c) S. F. Martin, Pure Appl. Chem. 2005, 77, 1207-11212.
45. G. C. Fu, S. T. Nguyen, R. H. Grubbs, J. Am. Chem. Soc. 1993, 115, 9856-9857.
46. A. Fürstner, J. Grabowski, C. W. Lehmann, J. Org. Chem. 1999, 64, 8275-8280.
47. The stereochemistry of 24b (cis-anti-cis) was assigned following extensive NMR analysis. See the Supporting Information for details.
48. We are very grateful to Professor Mary Garson (University of Queensland) for providing an authentic sample of dihydrohaliclonacyclamine C.
49. CCDC 744717 (25) contains 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.
50. a) S. Ohira, Synth. Commun. 1989, 19, 561-564;
51. b) S. Müller, B. Liepold, G. J. Roth, H. J. Bestmann, Synlett 1996, 521-522.
52. M. Bindl, R. Stade, E. K. Heilmann, A. Picot, R. Goddard, A. Fürstner, J. Am. Chem. Soc. 2009, 131, 9468-9470.