Enantioselective synthesis of (+)-isolysergol via ring-closing metathesis

Organic Letters

Volumn 12, Issue 11, 2010, Pages 2610-2613

  Deck, Jason A ^a   Martin, Stephen F ^a  

^a UNIVERSITY OF TEXAS AT AUSTIN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ERGOLINE DERIVATIVE; LYSERGOL; MOLYBDENUM;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; MICROWAVE RADIATION; STEREOISOMERISM; SYNTHESIS;

CATALYSIS; CYCLIZATION; ERGOLINES; MICROWAVES; MOLECULAR STRUCTURE; MOLYBDENUM; STEREOISOMERISM;

EID: 77953015306     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol100819f     Document Type: Article

References (54)

1. For a general review of olefin metathesis and its applications, see
2. Handbook of Metathesis; Grubbs, R. H., Ed.; Wiley-VCH: Weinheim, 2003; Vols. 1-3.
3. For a general review of applications of RCM to the synthesis of oxygen and nitrogen heterocycles, see
4. Deiters, A.; Martin, S. F. Chem. Rev. 2004, 104, 2199-2238
5. See for example
6. Martin, S. F. In Handbook of Metathesis; Grubbs, R. H., Ed.; Wiley-VCH: Weinheim, 2003, Vol. 2, pp 338 - 352
7. See also: Martin, S. F.; Liao, Y.; Wong, Y.; Rein, T. Tetrahedron Lett. 1994, 35, 691-694
8. Martin, S. F.; Liao, Y.; Chen, H.-J.; Pätzel, M.; Ramser, M. N. Tetrahedron Lett. 1994, 35, 6005-6008
9. Martin, S. F.; Chen, H.-J.; Courtney, A. K.; Liao, Y.; Pätzel, M.; Ramser, M. N.; Wagman, A. S. Tetrahedron 1996, 52, 7251-7264
10. Neipp, C. E.; Martin, S. F. J. Org. Chem. 2003, 68, 8867-8878
11. Simila, S. T. M.; Martin, S. F. J. Org. Chem. 2007, 72, 5342-5349
12. For selected references, see
13. Fellows, I. M.; Kaelin, D. E., Jr.; Martin, S. F. J. Am. Chem. Soc. 2000, 122, 10781-10787
14. Humphrey, J. M.; Liao, Y.; Ali, A.; Rein, T.; Wong, Y.-L.; Chen, H.-J.; Courtney, A. K.; Martin, S. F. J. Am. Chem. Soc. 2002, 124, 8584-8592
15. Washburn, D. G.; Heidebrecht, R. W., Jr.; Martin, S. F. Org. Lett. 2003, 5, 3523-3525
16. Brenneman, J. B.; Machauer, R.; Martin, S. F. Tetrahedron 2004, 60, 7301-7314
17. Andrade, R. B.; Martin, S. F. Org. Lett. 2005, 7, 5733-5735
18. Deiters, A.; Pettersson, M.; Martin, S. F. J. Org. Chem. 2006, 71, 6547-6561
19. Kummer, D. A.; Brenneman, J. B.; Martin, S. F. Tetrahedron 2006, 62, 11437-11449
20. Mukherjee, J.; Menge, M. Adv. Biochem. Eng. Biotechnol. 2000, 68, 1-20
21. For selected syntheses of and approaches to lysergic acid, see
22. Kornfield, E. C.; Fornefeld, E. J.; Kline, G. B.; Mann, M. J.; Morrison, D. E.; Jones, R. G.; Woodward, R. B. J. Am. Chem. Soc. 1956, 78, 3087-3114
23. Oppolzer, W.; Francotte, E.; Battig, K. Helv. Chim. Acta 1981, 64, 478-481
24. Rebek, J., Jr.; Tai, D. F.; Shue, Y.-K. J. Am. Chem. Soc. 1984, 106, 1813-1819
25. Ninomiya, I.; Hashimoto, C.; Kiguchi, T.; Naito, T. J. Chem. Soc., Perkin Trans. 1 1985, 941-948
26. Cacchi, S.; Ciattini, P. G.; Morera, E.; Ortar, G. Tetrahedron Lett. 1988, 29, 3117-3120
27. Saai, C.; Crotts, D. D.; Hsu, G.; Vollhardt, K. P. C. Synlett 1994, 487-489
28. Özlü, Y.; Cladingboel, D. E.; Parsons, P. J. Tetrahedron 1994, 50, 2183-2206
29. Barbey, S.; Mann, J. Synlett 1995, 27-28
30. Marino, J. P., Jr.; Osterhout, M. H.; Padwa, A. J. Org. Chem. 1995, 60, 2704-2713
31. Ralbovsky, J. L.; Scola, P. M.; Sugino, E.; Burgos-Garcia, C.; Weinreb, S. M.; Parvez, M. Heterocycles 1996, 43, 1497-1512
32. Moldvai, I.; Temesvari-Major, E.; Incze, M.; Szentirmay, E.; Gaics-Baitz, E.; Szaintay, C. J. Org. Chem. 2004, 69, 5993-6000
33. Hendrickson, J. B.; Wang, J. Org. Lett. 2004, 6, 3-5
34. Inoue, T.; Yokoshima, S.; Fukuyama, T. Heterocycles 2009, 79, 373-378
35. Kurokawa, T.; Isomura, M.; Tokuyama, H.; Fukuyama, T. Synlett 2009, 775-777
36. For a review of ARCM, see
37. Schrock, R. R.; Hoveyda, A. H. Angew. Chem., Int. Ed. 2003, 42, 4592-4633
38. Lee, K. L.; Goh, J. B.; Martin, S. F. Tetrahedron Lett. 2001, 42, 1635-1638
39. Yokoyama, Y.; Matsumoto, T.; Murakami, Y. J. Org. Chem. 1995, 60, 1486-1487
40. Dickson, H. D.; Smith, S. C.; Hinkle, K. W. Tetrahedron Lett. 2004, 45, 5597-5599
41. For related additions, see
42. Courtois, G.; Harama, M.; Miginiac, P. J. Organomet. Chem. 1981, 218, 275-298
43. Alvaro, G.; Grepioni, F.; Grilli, S.; Maini, L.; Martelli, G.; Savoia, D. Synthesis 2000, 581-587
44. For some recent leading references, see
45. Michaut, A.; Boddaert, T.; Coquerel, Y.; Rodriguez, J. Synthesis 2007, 2867-2871
46. Coquerel, Y.; Rodriguez, J. Eur. J. Org. Chem. 2008, 1125-1132
47. Nicks, F.; Borguet, Y.; Delfosse, S.; Bicchielli, D.; Delaude, L.; Sauvage, X.; Demonceau, A. Aust. J. Chem. 2009, 62, 184-207
48. Alexander, J. B.; La, D. S.; Cefalo, D. R.; Hoveyda, A. H.; Schrock, R. R. J. Am. Chem. Soc. 1998, 120, 4041-4042
49. Lysergaldehyde has not been characterized, and the few reports dealing with it or derivatives thereof describe only difficulties in formation of the aldehyde. For examples, see
50. Lin, C.-C. L.; Blair, G. E.; Cassady, J. M.; Gröger, D.; Maier, W.; Floss, H. G. J. Org. Chem. 1973, 38, 2249-2251
51. Choong, T. C.; Thompson, B. L.; Shough, H. R. J. Pharm. Sci. 1977, 66, 1340-1341
52. Donohoe, T. J.; Moore, P. R.; Waring, M. J. Tetrahedron Lett. 1997, 38, 5027-5030
53. Ninomiya, I.; Hashimoto, C.; Kiguchi, T.; Naito, T.; Barton, D. H. R.; Lusinchi, X.; Milliet, P. J. Chem. Soc., Perkin Trans. 1 1990, 707-713
54. Inuki, S.; Oishi, S.; Fujii, N.; Ohno, H. Org. Lett. 2008, 10, 5239-5242