Unified route to asymmetrically substituted butenolide, maleic anhydride, and maleimide constituents of Antrodia camphorata

Tetrahedron

Volumn 68, Issue 47, 2012, Pages 9592-9597

  Boukouvalas, John ^a   Albert, Vincent ^a   Loach, Richard P ^a   Lafleur Lambert, Raphaël ^a  

^a UNIVERSITÉ LAVAL   (Canada)

Author keywords

Hydroxybutenolide; Cross coupling; Dimethyldioxirane; Furan; Oxidation

Indexed keywords

4 HYDROXYPHENYLACETIC ACID; ANTINEOPLASTIC AGENT; ANTROCINNAMOMIN D; ANTRODIN A; ANTRODIN B; BUTENOLIDE; CHINESE DRUG; FURAN DERIVATIVE; HERBACEOUS AGENT; IRON; MALEIC ANHYDRIDE; MALEIMIDE; UNCLASSIFIED DRUG;

ANTRODIA CAMPHORATA; ARTICLE; ASYMMETRIC CATALYSIS; COMMERCIAL PHENOMENA; CONTROLLED STUDY; CROSS COUPLING REACTION; NONHUMAN; PRIORITY JOURNAL; SUBSTITUTION REACTION;

TAIWANOFUNGUS CAMPHORATUS;

EID: 84867497192     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2012.09.064     Document Type: Article

References (91)

1. Z.-H. Ao, Z.-H. Xu, Z.-M. Lu, H.-Y. Xu, X.-M. Zhang, and W.-F. Dou J. Ethnopharmacol. 121 2009 194 212
2. Y.-C. Chen, H.-O. Ho, C.-H. Su, and M.-T. Sheu J. Exp. Clin. Med. 2 2010 274 281
3. C.-H. Huang, Y.-J. Chen, and C.-C. Lin Curr. Top. Neutraceut. Res. 10 2012 61 74
4. P.Y.-K. Yue, T.Y.-K. Chan, C.K.-M. Law, Y.-K. Tsoi, and K.S.-Y. Leung Int. J. Med. Mushrooms 14 2012 241 256
5. Y.-C. Du, F.-R. Chang, T.-Y. Wu, Y.-M. Hsu, M. El-Shazly, C.-F. Chen, P.-J. Sung, Y.-Y. Lin, Y.-H. Lin, Y.-C. Wu, and M.-C. Lu Phytomedicine 19 2012 788 796
6. N. Nakamura, A. Hirakawa, J.-J. Gao, H. Kakuda, M. Shiro, Y. Komatsu, C.-c. Sheu, and M. Hattori J. Nat. Prod. 67 2004 46 48
7. 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
8. S.-C. Chien, M.-L. Chen, H.-T. Kuo, Y.-C. Tsai, B.-F. Lin, and Y.-H. Kuo J. Agric. Food Chem. 56 2008 7017 7022
9. C.-L. Wen, C.-L. Teng, C.-H. Chiang, C.-C. Chang, W.-L. Hwang, S.-L. Hsu, J.-S. Denge, G.-J. Huang, C.-L. Kuo, and S.-L. Hsu Phytomedicine 19 2012 424 435
10. D.T. Phuong, C.-M. Ma, M. Hattori, and J.S. Jin Phytother. Res. 23 2009 582 584
11. C.-L. Wen, C.-C. Chang, S.-S. Huang, C.-L. Kuo, S.-L. Hsu, J.-S. Deng, and G.-J. Huang J. Ethnopharmacol. 137 2011 575 584
12. For a pharmacokinetic study of antrodins B and C, see: Y. Liu, X. Di, X. Liu, W. Shen, and K.S.-Y. Leung J. Pharm. Biomed. Anal. 53 2010 781 784
13. E.-L. Lin, Y.-J. Lee, S.-M. Wang, P.-Y. Huang, and T.-H. Tseng Eur. J. Pharmacol. 680 2012 8 15
14. M.M. Baag, and N.P. Argade Synthesis 2006 1005 1008
15. S.G. Stewart, M.E. Polomska, and R.W. Lim Tetrahedron Lett. 48 2007 2241 2244
16. S.G. Stewart, L.A. Ho, M.E. Polomska, A.T. Percival, and G.C.T. Yeoh ChemMedChem 4 2009 1657 1667
17. C.-F. Cheng, Z.-C. Lai, and Y.-J. Lee Tetrahedron 64 2008 4347 4353
18. P. Sellès Org. Lett. 7 2005 605 608
19. D. Basavaiah, B. Devendar, K. Aravindu, and A. Veerendhar Chem. - Eur. J. 16 2010 2031 2035
20. S. Prateeptongkum, K.M. Driller, R. Jackstell, and M. Beller Chem. Asian J. 5 2010 2173 2176
21. D.L.J. Clive, Minaruzzaman, and L. Ou J. Org. Chem. 70 2005 3318 3320 and Supporting information
22. H. Fujimoto, Y. Satoh, K. Yamaguchi, and M. Yamazaki Chem. Pharm. Bull. 46 1998 1506 1510
23. H. Fujimoto, T. Asai, Y.-P. Kim, and M. Ishibashi Chem. Pharm. Bull. 54 2006 550 553
24. B. Clark, R.J. Capon, E. Lacey, S. Tennant, J.H. Gill, B. Bulheller, and G. Bringmann J. Nat. Prod. 68 2005 1226 1230 and cited refs
25. T. Momose, G. Tanabe, H. Tsujimori, and O. Muraoka Chem. Pharm. Bull. 40 1992 2525 2530
26. For recent syntheses of anhydride 8, which is also a fungal metabolite, see Ref. 15b and the following article: M.M. Baag, and N.P. Argade Synthesis 2008 26 28
27. N. Kornblum, and H.E. DeLaMare J. Am. Chem. Soc. 73 1951 880 881
28. C.W. Jefford, S. Kohmoto, J.-C. Rossier, and J. Boukouvalas J. Chem. Soc., Chem. Commun. 1985 1783 1784
29. C.W. Jefford, J.-C. Rossier, and J. Boukouvalas J. Chem. Soc., Chem. Commun. 1986 1701 1702
30. S.T. Staben, X. Linghu, and F.D. Toste J. Am. Chem. Soc. 126 2006 12658 12659
31. K.C. Nicolaou, S. Totokotsopoulos, D. Giguère, Y.-P. Sun, and D. Sarlah J. Am. Chem. Soc. 133 2011 8150 8153
32. G.S. Buchanan, K.P. Cole, Y. Tang, and R.P. Hsung J. Org. Chem. 76 2011 7027 7039
33. H. Tan, X. Chen, Z. Liu, and D.Z. Wang Tetrahedron 68 2012 3952 3955
34. M.J. Palframan, G. Kociok-Köhn, and S.E. Lewis Chem. - Eur. J. 18 2012 4766 4774
35. M.R. Kernan, and D.J. Faulkner J. Org. Chem. 53 1988 2773 2776
36. A. Mallinger, T. Le Gall, and C. Mioskowski J. Org. Chem. 74 2009 1124 1129
37. A. Mallinger, T. Le Gall, and C. Mioskowski Synlett 2008 386 388
38. J. Boukouvalas, N. Lachance, M. Ouellet, and M. Trudeau Tetrahedron Lett. 39 1998 7665 7668
39. F. Bellina, C. Anselmi, and R. Rossi Tetrahedron Lett. 42 2001 3851 3854
40. J. Zhang, P.G. Blazecka, D. Belmont, and J.G. Davidson Org. Lett. 4 2002 4559 4561
41. D.R. Williams, A.L. Nold, and R.J. Mullins J. Org. Chem. 69 2004 5374 5382
42. J. Boukouvalas, and M. Pouliot Synlett 2005 343 345
43. R. Le Vézouët, A.J.P. White, J.N. Burrows, and A.G.M. Barrett Tetrahedron 62 2006 12252 12263
44. S. Chen, and R.W. Williams Tetrahedron 62 2006 11572 11579
45. J. Boukouvalas, S. Côté, and B. Ndzi Tetrahedron Lett. 48 2007 105 107
46. J. Boukouvalas, P.P. Beltrán, N. Lachance, S. Côté, F. Maltais, and M. Pouliot Synlett 2007 219 222
47. R. De Simone, R.M. Andrés, M. Aquino, I. Bruno, M.D. Guerrero, M.C. Terencio, M. Paya, and R. Riccio Chem. Biol. Drug Des. 76 2010 17 24
48. J. Boukouvalas, and V. Albert Synlett 2011 2541 2544
49. R. Zhang, G. Iskander, P. da Silva, D. Chan, V. Vignevich, V. Nguyen, M.M. Bhadbhade, D.S. Black, and N. Kumar Tetrahedron 67 2011 3010 3016
50. L.C.A. Barbosa, J.O.S. Varejão, D. Petrollino, P.F. Pinheiro, A.J. Demuner, C.R.A. Maltha, and G. Forlani Arkivoc 5 2012 15 32
51. R. Grigg, P. Kennewell, and V. Savic Tetrahedron 50 1994 5489 5494
52. T. Honda, H. Mizutani, and K. Kanai J. Org. Chem. 61 1996 9374 9378
53. M.-L. Yao, and M.-Z. Deng J. Org. Chem. 65 2000 5034 5036
54. G.A. Molander, and D.J. St. Jean Jr. J. Org. Chem. 67 2002 3861 3865
55. N. Zorn, and R. Lett Tetrahedron Lett. 47 2006 4325 4330
56. J.S. Clark, J.M. Northall, F. Marlin, B. Nay, C. Wilson, A.J. Blake, and M.J. Waring Org. Biomol. Chem. 6 2008 4012 4025
57. J. Boukouvalas, and L.C. McCann Tetrahedron Lett. 51 2010 4636 4639
58. C. Ghobril, J. Kister, and R. Baati Eur. J. Org. Chem. 2011 3416 3419
59. R.J. Duffy, K.A. Morris, R. Vallakati, W. Zhang, and D. Romo J. Org. Chem. 74 2009 4772 4781
60. A notable exception is the parent β-bromobutenolide, routinely prepared from β-tetronic acid in >80% yield (e.g., Refs. 23a and f) by the method of Jas: G. Jas Synthesis 1991 965 966
61. B. Scheiper, M. Bonnekessel, H. Krause, and A. Fürstner J. Org. Chem. 69 2004 3943 3949
62. A. Fürstner, H. Krause, and C.W. Lehmann Angew. Chem., Int. Ed. 45 2006 440 444
63. A. Fürstner, R. Martin, H. Krause, G. Seidel, R. Goddard, and C.W. Lehmann J. Am. Chem. Soc. 130 2008 8773 8787
64. M. Tamura, and J. Kochi J. Am. Chem. Soc. 93 1971 1488 1489
65. M. Tamura, and J. Kochi Synthesis 1971 303 305
66. B. Bhayana, B.P. Fors, and S.L. Buchwald Org. Lett. 11 2009 3954 3957
67. A. Suzuki, and Y. Yamamoto Chem. Lett. 40 2011 894 901
68. 2 with α,β-dibromobutenolide, see: F. Bellina, and R. Rossi Synthesis 2002 2729 2732
69. G. Zou, Y.K. Reddy, and J.R. Falck Tetrahedron Lett. 42 2001 7213 7215
70. D.A. Nicoll-Griffith, J.A. Yergey, L.A. Trimble, J.M. Silva, C. Li, N. Chauret, J.Y. Gauthier, E. Grimm, S. Leger, P. Roy, M. Thérien, Z. Wang, P. Prasit, R. Zamboni, R.N. Young, C. Brideau, C.-C. Chan, J. Mancini, and D. Riendeau Bioorg. Med. Chem. Lett. 10 2000 2683 2686
71. W.C. Black, C. Brideau, C.-C. Chan, S. Charleson, W. Cromlish, R. Gordon, E.L. Grimm, G. Hughes, S. Leger, C.-S. Li, D. Riendeau, M. Thérien, Z. Wang, L.-J. Xu, and P. Prasit Bioorg. Med. Chem. Lett. 13 2003 1195 1198
72. C. Lamberth, E. Godineau, T. Smejkal, and S. Trah Tetrahedron Lett. 53 2012 4117 4120
73. J. Boukouvalas, and N. Lachance Synlett 1998 31 32
74. J. Boukouvalas, Y.-X. Cheng, and J. Robichaud J. Org. Chem. 63 1998 228 229
75. J. Boukouvalas, and Y.-X. Cheng Tetrahedron Lett. 39 1998 7025 7026
76. I.S. Marcos, A.B. Pedrero, M.J. Sexmero, D. Diez, P. Basabe, F.A. Hernández, and J.G. Urones Tetrahedron Lett. 44 2003 369 372
77. I.S. Marcos, A.B. Pedrero, M.J. Sexmero, D. Diez, N. García, M.A. Escola, P. Basabe, A. Conde, R.F. Moro, and J.G. Urones Synthesis 2005 3301 3310
78. J. Boukouvalas, J. Robichaud, and F. Maltais Synlett 2006 2480 2482
79. J. Boukouvalas, J.-X. Wang, O. Marion, and B. Ndzi J. Org. Chem. 71 2006 6670 6673
80. J. Boukouvalas, and R.P. Loach J. Org. Chem. 73 2008 8109 8112
81. J. Boukouvalas, and L.C. McCann Tetrahedron Lett. 52 2011 1202 1204
82. M. Yamashita, T. Yamashita, and S. Aoyagi Org. Lett. 13 2011 2204 2207
83. T. Yamashita, M. Yamashita, and S. Aoyagi Tetrahedron Lett. 52 2011 4266 4268
84. J. Boukouvalas, and V. Albert Tetrahedron Lett. 53 2012 3027 3029
85. J. Boukouvalas, Y. Xiao, Y.-X. Cheng, and R.P. Loach Synlett 2007 3198 3200
86. J. Boukouvalas, R.P. Loach, and E. Ouellet Tetrahedron Lett. 52 2011 5047 5050
87. Both naturally derived and synthetic antrocinnamomin D are optically inactive. The individual enantiomers of such γ-hydroxybutenolides are known to undergo facile interconversion 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
88. W.H. Miles, and M. Yan Tetrahedron Lett. 51 2010 1710 1712
89. P.D. Davis, and R.A. Bit Tetrahedron Lett. 31 1990 5201 5204
90. W. Adam, J. Bialas, and L. Hadjiarapoglou Chem. Ber. 124 1991 2377
91. R.W. Murray, and M. Singh Org. Synth. 74 1997 91 100