Concise, regiocontrolled synthesis of yangjinhualine A

Tetrahedron Letters

Volumn 52, Issue 11, 2011, Pages 1202-1204

  Boukouvalas, John ^a   McCann, Lucas C ^a  

^a UNIVERSITÉ LAVAL   (Canada)

Author keywords

Dimethyldioxirane; Furan; Lactone; Natural product synthesis; Oxidation

Indexed keywords

BUTENOLIDE; FURAN DERIVATIVE; SILICON DERIVATIVE; UNCLASSIFIED DRUG; YANGJINHUALINE A;

ARTICLE; CHEMICAL REACTION; CHINESE HERB; DATURA METEL; DRUG ISOLATION; DRUG STRUCTURE; DRUG SYNTHESIS; NONHUMAN; REACTION ANALYSIS; SILYLATION; SUZUKI REACTION;

DATURA METEL;

EID: 79751534362     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2011.01.036     Document Type: Article

References (62)

1. Chinese Pharmacopoeia, Shanghai Science and Technology Press, Shanghai, 1986; Vol. 2, pp 1719-1722.
2. M. Hassan, F.M.S. Azam, S.S. Shampa, S. Mahajebin, K.Z.G. Ara, R. Jahan, and M. Rahmatullah J. Biotechnol. 136 Suppl. 1 2008 S162 S163
3. H. Kuang, B. Yang, L. Tang, Y. Xia, and D. Dou Helv. Chim. Acta 92 2009 1315 1323
4. B.-Y. Yang, Y.-G. Xia, Q.-H. Wang, D.-Q. Dou, and H.-X. Kuang Fitoterapia 81 2010 1003 1005
5. H. Kuang, B. Yang, Y. Xia, and W. Feng Arch. Pharm. Res. 31 2008 1094 1097
6. K. Jenett-Siems, K. Siems, J. Jakupovic, P.N. Solis, M.P. Gupta, F.P. Mockenhaupt, U. Bienzle, and E. Eich Planta Med. 66 2000 384 385
7. G. Grossmann, M. Poncioni, M. Bornand, B. Jolivet, M. Neuburger, and U. Séquin Tetrahedron 59 2003 3237 3251
8. T. Hosoe, K. Fukushima, T. Itabashi, K. Nozawa, K. Takizawa, and K. Kawai Heterocycles 63 2004 2581 2589
9. T. Kamo, M. Matsue, M. Kashiwabara, and M. Hirota Biosci. Biotechnol. Biochem. 70 2006 2307 2309
10. C. Clarkson, E.V. Madikane, S.H. Hansen, P.J. Smith, and J.W. Jaroszewski Planta Med. 73 2007 578 584
11. K.H. Kim, H.J. Noh, S.C. Choi, K.M. Park, S.-J. Seok, and K.R. Lee Bioorg. Med. Chem. Lett. 20 2010 5385 5388
12. T. Hosoe, J.B. Gloer, D.T. Wicklow, H.A. Raja, and C.A. Shearer Heterocycles 81 2010 2123 2130
13. Y.-C. Lin, A.E. Fazary, and Y.-C. Shen Tetrahedron Lett 51 2010 6654 6657
14. D +5.2 (Ref. 3), γ-hydroxybutenolides lacking additional asymmetric centers are usually isolated as optically inactive compounds (e.g., 2-4, Refs. 6,7 ). Epimerization readily occurs via their open-chain tautomers: W.H. Miles, D.G. Duca, B.R. Selfridge, C.A.P. De Sousa, K.B. Hamman, E.O. Goodzeit, and J.T. Freedman Tetrahedron Lett 48 2007 7809 7812
15. W.H. Miles, and M. Yan Tetrahedron Lett 51 2010 1710 1712
16. M.-D. Wu, M.-J. Cheng, B.-C. Wang, Y.-J. Yech, J.-T. Lai, Y.-H. Kuo, G.-F. Yuan, and I.-S. Chen J. Nat. Prod. 71 2008 1258 1261
17. H. Fujimoto, T. Asai, Y.-P. Kim, and M. Ishibashi Chem. Pharm. Bull. 54 2006 550 553
18. Y.-J. Xu, C-P. Tang, M.-J. Tan, C.-Q. Ke, T. Wu, and Y. Ye Chem. Biodivers. 7 2010 151 157
19. M.J. Alcaraz, and M. Payá Curr. Opin. Invest. Drugs 7 2006 974 979
20. S.S. Ebada, W.H. Lin, and P. Proksch Mar. Drugs 8 2010 313 346
21. F. Folmer, M. Jaspars, M. Schumacher, M. Dicato, and M. Diederich Biochem. Pharmacol. 80 2010 1793 1800
22. D.J. Faulkner, D.J. Newman, and G.M. Cragg Nat. Prod. Rep. 21 2004 50 76
23. D.J. Newman, and G.M. Cragg J. Nat. Prod. 67 2004 1216 1238
24. P.P. Reddy, A.K. Tiwari, R.R. Rao, K. Madhusudhana, V.R.S. Rao, A.Z. Ali, K.S. Babu, and J.M. Rao Bioorg. Med. Chem. Lett. 19 2009 2562 2565
25. Select examples: A. Pommier, V. Stepanenko, K. Jarowicki, and P.J. Kocienski J. Org. Chem. 68 2003 4008 4013
26. D. Demeke, and C.J. Forsyth Org. Lett. 5 2003 991 994
27. P. Basabe, S. Delgado, I.S. Marcos, D. Diez, A. Diego, M. De Román, and J.G. Urones J. Org. Chem. 70 2005 9480 9485
28. M. Aquino, I. Bruno, R. Riccio, and L. Gomez-Paloma Org. Lett. 8 2006 4831 4834
29. R. Murelli, A.K. Cheung, and M.L. Snapper J. Org. Chem. 72 2007 1545 1552
30. S.N. Patil, B.E. Stephens, and F. Liu Tetrahedron 64 2008 10831 10836
31. M. Oshida, M. Ono, A. Nakazaki, and S. Kobayashi Heterocycles 80 2010 313 328
32. L.-Z. Liu, J.-C. Han, G.-Z. Yue, C.-C. Li, and Z. Yang J. Am. Chem. Soc. 132 2010 13608 13609
33. R.S. Bon, and H. Waldmann Acc. Chem. Res. 43 2010 1103 1114
34. For our own work on the synthesis of γ-hydroxybutenolides, see: J. Boukouvalas, and N. Lachance Synlett 1998 31 32
35. J. Boukouvalas, Y.-X. Cheng, and J. Robichaud J. Org. Chem. 63 1998 228 229
36. J. Boukouvalas, J.-X. Wang, O. Marion, and B. Ndzi J. Org. Chem. 71 2006 6670 6673
37. J. Boukouvalas, J. Robichaud, and F. Maltais Synlett 2006 2480 2482
38. J. Boukouvalas, and R.P. Loach J. Org. Chem. 73 2008 8109 8112
39. Y. Ichikawa, K. Tsuboi, A. Naganawa, and M. Isobe Synlett 1993 907 908
40. K. Tsuboi, Y. Ichikawa, Y. Jiang, A. Naganawa, and M. Isobe Tetrahedron 53 1997 5123 5142
41. M.A. Castro, J.M. Miguel del Corral, M. Gordaliza, P.A. García, M.A. Gómez-Zurita, and A. San Feliciano Bioorg. Med. Chem. 15 2007 1670 1678
42. D.L.J. Clive, Minaruzzaman, and L. Ou J. Org. Chem. 70 2005 3318 3320 and Supporting Information
43. E.M. Beccalli, E. Erba, and P. Trimarco Synth. Commun. 30 2000 629 641
44. J. Boukouvalas, P.P. Beltrán, N. Lachance, S. Côté, F. Maltais, and M. Pouliot Synlett 2007 219 222
45. R. Grigg, P. Kennewell, and V. Savic Tetrahedron 50 1994 5489 5494
46. N. Zorn, and R. Lett Tetrahedron Lett 47 2006 4325 4330
47. R.J. Duffy, K.A. Morris, R. Vallakati, W. Zhang, and D. Romo J. Org. Chem. 74 2009 4772 4781
48. J. Boukouvalas, N. Lachance, M. Ouellet, and M. Trudeau Tetrahedron Lett 39 1998 7665 7668
49. M.-L. Yao, and M.-Z. Deng J. Org. Chem. 65 2000 5034 5036
50. J. Zhang, P.G. Blazecka, D. Belmont, and J.G. Davidson Org. Lett. 4 2002 4559 4561
51. B. Scheiper, M. Bonnekessel, H. Krause, and A. Fürstner J. Org. Chem. 69 2004 3943 3949
52. J. Boukouvalas, and M. Pouliot Synlett 2005 343 345
53. J. Boukouvalas, S. Côté, and B. Ndzi Tetrahedron Lett 48 2007 105 107
54. J. Boukouvalas, and L.C. McCann Tetrahedron Lett 51 2010 4636 4639
55. U.K. Tambar, T. Kano, J.F. Zepernick, and B.M. Stoltz J. Org. Chem. 71 2006 8357 8364
56. 13C NMR data have not been reported (Refs. 17a,b ).
57. 3Si (m/z): 304.1495, Found: 304.1486.
58. 2 (m/z): 460.2829, Found: 460.2837.
59. For some related synthetic applications of DMDO, see: J. Boukouvalas, and Y.-X. Cheng Tetrahedron Lett 39 1998 7025 7026
60. B.B. Snider, and B.J. Neubert J. Org. Chem. 69 2004 8952 8955
61. J. Boukouvalas, Y. Xiao, Y.-X. Cheng, and R.P. Loach Synlett 2007 3198 3200
62. 4 (m/z): 206.0579, Found: 206.0579.