Convergent total syntheses of the pentacyclic lamellarins K, T, U and W via the addition of azomethine ylides to tethered tolans

Heterocycles

Volumn 84, Issue 2, 2012, Pages 1141-1170

  Flynn, Bernard L ^a   Banwell, Martin G ^a  

^a AUSTRALIAN NATIONAL UNIVERSITY   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84856521419     PISSN: 03855414     EISSN: 18810942     Source Type: Journal    
DOI: 10.3987/COM-11-S(P)95     Document Type: Article

References (54)

1. For reviews and recent key papers on the isolation, synthesis and/or biology of the lamellarins and related compounds see: D. Pla, F. Albericio, and M. Álvarez, Med. Chem. Commun., 2011, 2, 689
2. T. Fukuda, F. Ishibashi, and M. Iwao, Heterocycles, 2011, 83, 491
3. Q. Li, J. Jiang, A. Fan, Y. Cui, and Y. Jia, Org. Lett., 2011, 13, 312
4. K. Hasse, A. C. Willis, and M. G. Banwell, Eur. J. Org. Chem., 2011, 88
5. P. Thipnate, M. Chittchang, N. Thasana, P. Saparpakorn, P. Ploypradith, and S. Hannongbua, Monatsh. Chem., 2011, 142, 97
6. C. Ballot, J. Kluza, S. Lancel, A. Martoriati, S. M. Hassoun, L. Mortier, J.-C. Vienne, G. Briand, P. Formstecher, C. Bailly, R. Nevìre, and P. Marchetti, Apoptosis, 2010, 15, 769
7. S. Boonya-udtayan, N. Yotapan, C. Woo, C. J. Bruns, S. Ruchirawat, and N. Thasana, Chem. Asian J., 2010, 5, 2113
8. M. Chittchang, M. P. Gleeson, P. Ploypradith, and S. Ruchirawat, Eur. J. Med. Chem., 2010, 45, 2165
9. M. Chittchang, P. Batsomboon, S. Ruchirawat, and P. Ploypradith, ChemMedChem., 2009, 4, 457
10. H. Fan, J. Peng, M. T. Hamann, and J.-F. Hu, Chem. Rev., 2008, 108, 264
11. J. Kluza, P. Marchetti, and C. Bailly, in Modern Alkaloids: Structure, Isolation, Synthesis and Biology, ed. by E. Fattorusso and O. Taglialatela-Scafati, Wiley-VCH, Weinheim, 2008, Chapter 7
12. D. Pla, F. Albericio, and M. Álvarez, Anti-Cancer Agents Med. Chem., 2008, 8, 746
13. D. Baunbak, N. Trinkler, Y. Ferandin, O. Lozach, P. Ploypradith, S. Rucirawat, F. Ishibashi, M. Iwao, and L. Meijer, Mar. Drugs, 2008, 6, 514
14. S. T. Handy and Y. Zhang, Org. Prep. Proced. Int., 2005, 37, 411
15. P. Cironi, F. Albericio, and M. Álvarez, Prog. Heterocycl. Chem., 2005, 16, 1
16. C. Bailly, Curr. Med. Chem.-Anti-Cancer Agents, 2004, 4, 363.
17. S. Urban, L. Hobbs, J. N. A. Hooper, and R. J. Capon, Aust. J. Chem., 1995, 48, 1491.
18. M. Banwell, B. Flynn, and D. Hockless, Chem. Commun., 1997, 2259. Aspects of the present work have also been disclosed in a patent
19. M. G. Banwell and B. L. Flynn, Preparation of Fused Polycyclic Alkaloids by Ring Closure of Azomethine Ylides, Novel Compounds Thereof and their Use as Chemotherapeutic Agents, Int. Patent No. WO 9850365, 1998; US Patent No. US7122673 B2, 2006.
20. A. R. Carroll, B. F. Bowden, and J. C. Coll, Aust. J. Chem., 1993, 46, 489.
21. P. Cironi, I. Manzanares, F. Albericio, and M. Álvarez, Org. Lett., 2003, 5, 2959
22. C. P. Ridley, M. V. R. Reddy, G. Rocha, F. D. Bushman, and D. J. Faulkner, Bioorg. Med. Chem., 2002, 10, 3285.
23. M. Díaz, E. Guitián, and L. Castedo, Synlett, 2001, 1164
24. M. Nyerges and L. Töke, Tetrahedron Lett., 2005, 46, 7531
25. S. Su and J. A. Porco Jr., J. Am. Chem. Soc., 2007, 129, 7744.
26. M. V. R. Reddy, D. J. Faulkner, Y. Venkateswarlu, and M. R. Rao, Tetrahedron, 1997, 53, 3457.
27. L. Kürti and B. Czakó, Strategic Applications of Named Reactions in Organic Synthesis, Elsevier, Amsterdam, 2005, pp. 424-425.
28. A. Arcadi, S. Cacchi, M. Del Rosario, G. Fabrizi, and F. Marinelli, J. Org. Chem., 1996, 61, 9280.
29. For a useful review on the intramolecular cycloaddition reactions of azomethine ylides, see: I. Coldham and R. Hufton, Chem. Rev., 2005, 105, 2765.
30. M. G. Banwell, B. L. Flynn, and S. G. Stewart, J. Org. Chem., 1998, 63, 9139
31. T. Sala and M. V. Sargent, J. Chem. Soc., Perkin Trans. 1, 1979, 2593
32. J. P. Gillespie, L. G. Amoros, and F. R. Stermitz, J. Org. Chem., 1974, 39, 3239
33. T. H. Simpson, J. Org. Chem., 1963, 28, 2107
34. C. Szántay, Acta Chim. Hung., 1957, 12, 83.
35. E. J. Corey and P. L. Fuchs, Tetrahedron Lett., 1972, 13, 3769.
36. J. Bourgeois, I. Dion, P. H. Cebrowski, F. Loiseau, A.-C. Bédard, and A. M. Beauchemin, J. Am. Chem. Soc., 2009, 131, 874.
37. M. G. Banwell, B. L. Flynn, A. C. Willis, and E. Hamel, Aust. J. Chem., 1999, 52, 767.
38. X. Wan and M. M. Joullié, J. Am. Chem. Soc., 2008, 130, 17236.
39. L. Kürti and B. Czakó, Strategic Applications of Named Reactions in Organic Synthesis, Elsevier, Amsterdam, 2005, pp. 202-203.
40. L. Kürti and B. Czakó, Strategic Applications of Named Reactions in Organic Synthesis, Elsevier, Amsterdam, 2005, pp. 348-349.
41. For related conversions, see: N. Sotomayor, E. Domínguez, and E. Lete, Tetrahedron, 1995, 51, 12721 and references cited therein.
42. For a useful and up-to-date commentary on this rearrangement, see: E. Jahnke and R. R. Tykwinski, Chem. Commun., 2010, 46, 3235.
43. L. Kürti and B. Czakó, Strategic Applications of Named Reactions in Organic Synthesis, Elsevier, Amsterdam, 2005, pp. 118-119.
44. Several other syntheses of lamellarin K have been reported: C. Peschko, C. Winklhofer, A. Terpin, and W. Steglich, Synthesis, 2006, 3048
45. P. Ploypradith, T. Petchmanee, P. Sahakitpichan, N. D. Litvinas, and S. Ruchirawat, J. Org. Chem., 2006, 71, 9440
46. M. Díaz, E. Guitián, and L. Castedo, Synlett, 2001, 1164.
47. Another synthesis of lamellarin T has been reported, see: Ref. 20b.
48. N. Thasana, B. Bjerke-Kroll, and S. Ruchirawat, Synlett, 2008, 505.
49. Several other syntheses of lamellarin U have been reported: (a) J. C. Liermann and T. Opatz, J. Org. Chem., 2008, 73, 4526
50. see Ref. 20b.
51. R. N. Warrener, L. Liu, and R. A. Russell, Tetrahedron, 1998, 54, 7485.
52. Another synthesis of lamellarin W has been reported, see: Ref. 20b.
53. Ruchirawat has demonstrated the utility of this reagent for generating pentacyclic lamellarins incorporating an unsaturated D-ring from their saturated counterparts, see: Ref. 20b.
54. W. C. Still, M. Kahn, and A. Mitra, J. Org. Chem., 1978, 43, 2923.