Chemical synthesis of the englerins

Chemistry - An Asian Journal

Volumn 7, Issue 1, 2012, Pages 22-35

  Pouwer, Rebecca H ^a   Richard, Jean Alexandre ^b   Tseng, Chih Chung ^c   Chen, David Y K ^d  

^a GRIFFITH UNIVERSITY   (Australia)

^b INSTITUTE OF CHEMICAL AND ENGINEERING SCIENCES   (Singapore)

^c NATIONAL CHIAO TUNG UNIVERSITY   (Taiwan)

^d Seoul National University   (South Korea)

Author keywords

cancer; guaianolide; natural products; sesquiterpene; total synthesis

Indexed keywords

CANCER; GUAIANOLIDE; NATURAL PRODUCTS; SESQUITERPENE; TOTAL SYNTHESIS;

DISEASES; PATIENT TREATMENT;

SYNTHESIS (CHEMICAL);

ANTINEOPLASTIC AGENT; ENGLERIN A; ENGLERIN B; SESQUITERPENE;

CELL PROLIFERATION; CHEMISTRY; DRUG EFFECT; HUMAN; NEOPLASM; PATHOLOGY; REVIEW; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

ANTINEOPLASTIC AGENTS; CELL PROLIFERATION; HUMANS; NEOPLASMS; SESQUITERPENES, GUAIANE; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84255169377     PISSN: 18614728     EISSN: 1861471X     Source Type: Journal    
DOI: 10.1002/asia.201100780     Document Type: Review

References (131)

1. E. Breitmaier, Terpenes, 2nd ed., Wiley-VCH, Weinheim, 2005
2. J. Gershenzon, N. Dudareva, Nat. Chem. Biol. 2007, 3, 408-414.
3. T. Hudlicky, J. W. Reed, The Way of Synthesis: Evolution of Design and Methods for Natural Products, Wiley-VCH, Weinheim, 2007. For a recent review on the synthesis of challenging terpenes, see
4. T. J. Maimone, P. S. Baran, Nat. Chem. Biol. 2007, 3, 396-407 and references therein.
5. For a recent review on the synthetic approaches to bicyclo[5.3.0]decane sesquiterpenes, see:, D. A. Foley, A. R. Maguire, Tetrahedron 2010, 66, 1131-1175.
6. R. Ratnayake, D. Covell, T. T. Ransom, K. R. Gustafson, J. A. Beutler, Org. Lett. 2009, 11, 57-60
7. J. A. Beutler, R. Ratnayake, D. Covell, T. R. Johnson, WO 2009/088854, 2009.
8. K. P. Chan, D. Y.-K. Chen, ChemMedChem 2011, 6, 420-423
9. L. Radtke, M. Willot, H. Sun, S. Ziegler, S. Sauerland, C. Strohmann, R. Fröhlich, P. Habenberger, H. Waldmann, M. Christmann, Angew. Chem. 2011, 123, 4084-4088
10. Angew. Chem. Int. Ed. 2011, 50, 3998-4002.
11. For a review on transannulation reactions in natural products synthesis, see:, P. A. Clarke, A. T. Reeder, J. Winn, Synthesis 2009, 691-709.
12. M. Willot, L. Radtke, D. Könning, R. Fröhlich, V. H. Gessner, C. Strohmann, M. Christmann, Angew. Chem. 2009, 121, 9269-9272
13. Angew. Chem. Int. Ed. 2009, 48, 9105-9108.
14. K. C. Nicolaou, P. G. Bulger, D. Sarlah, Angew. Chem. 2005, 117, 4564-4601
15. Angew. Chem. Int. Ed. 2005, 44, 4490-4527
16. A. Gradillas, J. Pérez-Castells, Angew. Chem. 2006, 118, 6232-6247
17. Angew. Chem. Int. Ed. 2006, 45, 6086-6101
18. A. Fürstner, Chem. Commun. 2011, 47, 6505-6511
19. J. Prunet, Eur. J. Org. Chem. 2011, 3634-3647.
20. M. Scholl, S. Ding, C. W. Lee, R. H. Grubbs, Org. Lett. 1999, 1, 953-957.
21. J. Inanaga, K. Hirata, H. Saeki, T. Katsuki, M. Yamaguchi, Bull. Chem. Soc. Jpn. 1979, 52, 1989-1993.
22. K. Molawi, N. Delpont, A. M. Echavarren, Angew. Chem. 2010, 122, 3595-3597
23. Angew. Chem. Int. Ed. 2010, 49, 3517-3519. For an analogy of this strategy with the terpene cyclase biosynthesis of terpenoids, see
24. M. Willot, M. Christmann, Nat. Chem. 2010, 2, 519-520.
25. A. S. K. Hashmi, G. J. Hutchings, Angew. Chem. 2006, 118, 8064-8105
26. Angew. Chem. Int. Ed. 2006, 45, 7896-7936
27. A. S. K. Hashmi, Chem. Rev. 2007, 107, 3180-3211
28. A. Fürstner, P. W. Davies, Angew. Chem. 2007, 119, 3478-3519
29. Angew. Chem. Int. Ed. 2007, 46, 3410-3449
30. D. J. Gorin, F. D. Toste, Nature 2007, 446, 395-403
31. E. Jime'nez-Nu'nâez, A. M. Echavarren, Chem. Commun. 2007, 333-346
32. E. Jime'nez-Nu'nâez, A. M. Echavarren, Chem. Rev. 2008, 108, 3326-3350
33. D. J. Gorin, B. D. Sherry, F. D. Toste, Chem. Rev. 2008, 108, 3351-3378. For a review on gold catalysis in total synthesis, see
34. A. S. K. Hashmi, M. Rudolph, Chem. Soc. Rev. 2008, 37, 1766-1775.
35. E. Jiménez-Núñez, C. K. Claverie, C. Nieto-Oberhuber, A. M. Echavarren, Angew. Chem. 2006, 118, 5578-5581
36. Angew. Chem. Int. Ed. 2006, 45, 5452-5455
37. E. Jiménez-Núñez, K. Molawi, A. M. Echavarren, Chem. Commun. 2009, 7327-7329
38. E. Jiménez-Núñez, M. Raducan, T. Lauterbach, K. Molawi, C. R. Solorio, A. M. Echavarren, Angew. Chem. 2009, 121, 6268-6271
39. Angew. Chem. Int. Ed. 2009, 48, 6152-6155.
40. T. Katsuki, K. B. Sharpless, J. Am. Chem. Soc. 1980, 102, 5974-5976. For a review, see
41. A. Pfenninger, Synthesis 1986, 89-116.
42. R. Appel, Angew. Chem. 1975, 87, 863-874
43. Angew. Chem. Int. Ed. Engl. 1975, 14, 801-811.
44. H. C. Kolb, M. S. VanNieuwenhze, K. B. Sharpless, Chem. Rev. 1994, 94, 2483-2547
45. P. Dupau, R. Epple, A. A. Thomas, V. V. Fokin, K. B. Sharpless, Adv. Synth. Catal. 2002, 344, 421-433. Nobel lecture
46. K. B. Sharpless, Angew. Chem. 2002, 114, 2126-2135
47. Angew. Chem. Int. Ed. 2002, 41, 2024-2032.
48. S. E. Denmark, R. A. Stavenger, J. Am. Chem. Soc. 2000, 122, 8837-8847.
49. C. H. M. Amijs, V. Lo'pez-Carrillo, M. Raducan, P. Pe'rez-Gala'n, C. Ferrer, A. M. Echavarren, J. Org. Chem. 2008, 73, 7721-7730.
50. P. Sundararaman, W. Herz, J. Org. Chem. 1977, 42, 813-819
51. W. G. Salmond, M. A. Barta, J. L. Havens, J. Org. Chem. 1978, 43, 2057-2059.
52. M. A. Umbreit, K. B. Sharpless, Org. Synth. 1981, 60, 29-32.
53. For a review on substrate-directable reactions, see:, A. H. Hoveyda, D. A. Evans, G. C. Fu, Chem. Rev. 1993, 93, 1307-1370.
54. B. Wüstenberg, A. Pfaltz, Adv. Synth. Catal. 2008, 350, 174-178.
55. Q. Zhou, X. Chen, D. Ma, Angew. Chem. 2010, 122, 3591-3594
56. Angew. Chem. Int. Ed. 2010, 49, 3513-3516.
57. R. W. Hoffmann, Synthesis 2006, 3531-3541
58. I. S. Young, P. S. Baran, Nat. Chem. 2009, 1, 193-205 and references therein.
59. A. Spaggiari, D. Vaccari, P. Davoli, G. Torre, F. Prati, J. Org. Chem. 2007, 72, 2216-2219.
60. M. A. Umbreit, K. B. Sharpless, J. Am. Chem. Soc. 1977, 99, 5526-5528.
61. J. D. More, N. S. Finney, Org. Lett. 2002, 4, 3001-3003.
62. S. V. Ley, J. Norman, W. P. Griffith, S. P. Marsden, Synthesis 1994, 639-666.
63. D. B. Dess, J. C. Martin, J. Org. Chem. 1983, 48, 4155-4156.
64. K. C. Nicolaou, Q. Kang, S. Y. Ng, D. Y. K. Chen, J. Am. Chem. Soc. 2010, 132, 8219-8222.
65. X. Du, F. Song, Y. Lu, H. Chen, Y. Liu, Tetrahedron 2009, 65, 1839-1845.
66. O. Achmatowicz, R. Bielski, Carbohydr. Res. 1977, 55, 165-176.
67. For a review on the cycloaddition of oxidopyrylium species in organic synthesis, see:, V. Singh, U. M. Krishna, Vikrant, G. K. Trivedi, Tetrahedron 2008, 64, 3405-3428.
68. P. A. Grieco, S. Gilman, M. Nishizawa, J. Org. Chem. 1976, 41, 1485-1486.
69. W. H. Clement, C. M. Selwitz, J. Org. Chem. 1964, 29, 241-243.
70. J. L. Luche, J. Am. Chem. Soc. 1978, 100, 2226-2227
71. G. A. Molander, Chem. Rev. 1992, 92, 29-68.
72. R. H. Crabtree, M. W. Davis, J. Org. Chem. 1986, 51, 2655-2661.
73. S. Nahm, S. M. Weinreb, Tetrahedron Lett. 1981, 22, 3815-3818.
74. A. Baeyer, V. Villiger, Ber. Dtsch. Chem. Ges. 1899, 32, 3625-3633. For a review, see
75. M. Renz, B. Meunier, Eur. J. Org. Chem. 1999, 737-750.
76. W. Oppolzer, C. Chapuis, G. Bernardinelli, Tetrahedron Lett. 1984, 25, 5885-5888.
77. V. Navickas, D. B. Ushakov, M. E. Maier, M. Ströbele, H.-J. Meyer, Org. Lett. 2010, 12, 3418-3421.
78. T. Ye, M. A. McKervey, Chem. Rev. 1994, 94, 1091-1160
79. A. Padwa, M. D. Weingarten, Chem. Rev. 1996, 96, 223-270
80. A. Padwa, Helv. Chim. Acta 2005, 88, 1357-1374
81. Z. Zhang, J. Wang, Tetrahedron 2008, 64, 6577-6605.
82. For a review, see, A. S. Kende, Org. React. 1960, 11, 261-316.
83. D. H. R. Barton, S. W. McCombie, J. Chem. Soc. Perkin Trans. 1 1975, 1574-1585.
84. P. A. S. Smith, Org. React. 1946, 3, 337-449
85. E. F. V. Scriven, K. Turnbull, Chem. Rev. 1988, 88, 297-368.
86. H. M. L. Davies, G. Ahmed, M. R. Churchill, J. Am. Chem. Soc. 1996, 118, 10774-10782.
87. J. Xu, E. J. E. Caro-Diaz, E. A. Theodorakis, Org. Lett. 2010, 12, 3708-3711.
88. G. M. Rubottom, M. A. Vazquez, D. R. Pelegrina, Tetrahedron Lett. 1974, 15, 4319-4322.
89. For a review, H. Stetter, Angew. Chem. 1976, 88, 695-704
90. Angew. Chem. Int. Ed. Engl. 1976, 15, 639-647.
91. E. M. Burgess, H. R. Penton, Jr., E. A. Taylor, J. Org. Chem. 1973, 38, 26-31. For a review, see
92. K. C. Nicolaou, S. A. Snyder, D. A. Longbottom, A. Z. Nalbandian, X. Huang, Chem. Eur. J. 2004, 10, 5581-5606.
93. B.-F. Sun, C.-L. Wang, R. Ding, J.-Y. Xu, G.-Q. Lin, Tetrahedron Lett. 2011, 52, 2155-2158. For selected reviews, see
94. H. M. R. Hoffmann, Angew. Chem. 1984, 96, 29-48
95. Angew. Chem. Int. Ed. Engl. 1984, 23, 1-19
96. J. H. Rigby, F. C. Pigge, Org. React. 1997, 51, 351-478
97. M. Harmata, Tetrahedron 1997, 53, 6235-6280
98. M. Harmata, Acc. Chem. Res. 2001, 34, 595-605
99. M. Harmata, P. Rashatasakhon, Tetrahedron 2003, 59, 2371-2395
100. M. Harmata, Adv. Synth. Catal. 2006, 348, 2297-2306.
101. I. V. Hartung, H. M. R. Hoffmann, Angew. Chem. 2004, 116, 1968-1984
102. Angew. Chem. Int. Ed. 2004, 43, 1934-1949
103. M. A. Battiste, P. M. Pelphrey, D. L. Wright, Chem. Eur. J. 2006, 12, 3438-3447.
104. T. H. Graham, B. D. Horning, D. W. C. MacMillan, Org. Synth. 2011, 88, 42-53.
105. R. M. Wilson, S. J. Danishefsky, J. Org. Chem. 2006, 71, 8329-8351
106. R. M. Wilson, S. J. Danishefsky, Acc. Chem. Res. 2006, 39, 539-549
107. K. Kumar, H. Waldmann, Angew. Chem. 2009, 121, 3272-3290
108. Angew. Chem. Int. Ed. 2009, 48, 3224-3242
109. R. M. Wilson, S. J. Danishefsky, Angew. Chem. 2010, 122, 6168-6193
110. Angew. Chem. Int. Ed. 2010, 49, 6032-6056
111. A. M. Szpilman, E. M. Carreira, Angew. Chem. 2010, 122, 9786-9823
112. Angew. Chem. Int. Ed. 2010, 49, 9592-9628.
113. D. B. Ushakov, V. Navickas, M. Ströbele, C. Maichle-Mössmer, F. Sasse, M. E. Maier, Org. Lett. 2011, 13, 2090-2093.
114. L. A. Paquette, Angew. Chem. 1990, 102, 642-660
115. Angew. Chem. Int. Ed. Engl. 1990, 29, 609-626
116. L. A. Paquette, Tetrahedron 1997, 53, 13971-14020.
117. K. Ishihara, M. Kubota, H. Kurihara, H. Yamamoto, J. Org. Chem. 1996, 61, 4560-4567.
118. M. P. Doyle, C. C. McOsker, N. Ball, C. T. West, J. Org. Chem. 1977, 42, 1922-1928
119. G. L. Larson, J. L. Fry, Org. React. 2008, 71, 1-737.
120. Z. Li, M. Nakashige, W. J. Chain, J. Am. Chem. Soc. 2011, 133, 6553-6556.
121. G. A. Molander, C. R. Harris, Chem. Rev. 1996, 96, 307-338
122. A. Krief, A.-M. Laval, Chem. Rev. 1999, 99, 745-777
123. H. B. Kagan, Tetrahedron 2003, 59, 10351-10372
124. K. Gopalaiah, H. B. Kagan, New J. Chem. 2008, 32, 607-637. For applications in the total synthesis of natural products, see
125. D. J. Edmonds, D. Johnston, D. J. Procter, Chem. Rev. 2004, 104, 3371-3403
126. K. C. Nicolaou, S. P. Ellery, J. S. Chen, Angew. Chem. 2009, 121, 7276-7301
127. Angew. Chem. Int. Ed. 2009, 48, 7140-7165
128. T. Nakata, Chem. Rec. 2010, 10, 159-172. For a highlight on the use of samarium(II) iodide in recent concise total syntheses, see
129. M. Szostak, D. J. Procter, Angew. Chem. 2011, 123, 7881-7883
130. Angew. Chem. Int. Ed. 2011, 50, 7737-7739.
131. For a recent review on the synthesis of englerin A, see:, W. J. Chain, Synlett 2011, 18, 2605-2608.