Phosphoric acid catalyzed desymmetrization of bicyclic bislactones bearing an all-carbon stereogenic center: Total syntheses of (-)-rhazinilam and (-)-leucomidine B

Angewandte Chemie - International Edition

Volumn 53, Issue 37, 2014, Pages 9926-9930

  Gualtierotti, Jean Baptiste ^a   Pasche, Delphine ^a   Wang, Qian ^a   Zhu, Jieping ^a  

^a EPFL   (Switzerland)

Author keywords

alkaloids; natural products; organocatalysis; synthetic methods; total synthesis

Indexed keywords

ALKALOIDS; CARBON; CATALYSIS; ENANTIOSELECTIVITY; REACTION KINETICS;

CATALYTIC AMOUNTS; DESYM-METRIZATION; ENANTIOSELECTIVE SYNTHESIS; NATURAL PRODUCTS; ORGANOCATALYSIS; STEREOGENIC CENTERS; SYNTHETIC METHODS; TOTAL SYNTHESIS;

SYNTHESIS (CHEMICAL);

EID: 84906949528     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201405842     Document Type: Article

References (111)

1. M. E. Kuehne, J. Am. Chem. Soc. 1964, 86, 2946.
2. L. Castedo, J. Harley-Mason, M. Kaplan, J. Chem. Soc. D 1969, 1444.
3. J.-Y. Laronze, J. Laronze-Fontaine, J. Lévy, J. Le Men, Tetrahedron Lett. 1974, 15, 491
4. A. Nemes, C. Szántay, Jr., L. Czibula, I. Greiner, ARKIVOC 2008, 154.
5. Aspidosperma family, see
6. G. Costello, J. E. Saxton, Tetrahedron 1986, 42, 6047
7. J. W. Blowers, J. E. Saxton, A. G. Swanson, Tetrahedron 1986, 42, 6071; Attempted synthesis of rhazinilam, see
8. C. Carité, J. P. Alazard, K. Ogino, C. Thal, Tetrahedron Lett. 1990, 31, 7011
9. J.-P. Alazard, C. Terrier, A. Mary, C. Thal, Tetrahedron 1994, 50, 6287.
10. M. Amat, M. Cantõ, N. Llor, V. Ponzo, M. Pérez, J. Bosch, Angew. Chem. 2002, 114, 345
11. Angew. Chem. Int. Ed. 2002, 41, 335
12. M. Amat, O. Bassas, N. Llor, M. Cantõ, M. Pérez, E. Molins, J. Bosch, Chem. Eur. J. 2006, 12, 7872.
13. J. C. F. Alves, A. B. C. Simas, P. R. R. Costa, J. D'Angelo, Tetrahedron: Asymmetry 1997, 8, 1963.
14. T. Gerfaud, C. Xie, L. Neuville, J. Zhu, Angew. Chem. 2011, 123, 4040
15. Angew. Chem. Int. Ed. 2011, 50, 3954
16. T. Buyck, Q. Wang, J. Zhu, Org. Lett. 2012, 14, 1338
17. T. Buyck, Q. Wang, J. Zhu, Angew. Chem. 2013, 125, 12946
18. Angew. Chem. Int. Ed. 2013, 52, 12714
19. Z. Xu, Q. Wang, J. Zhu, Angew. Chem. 2013, 125, 3354
20. Angew. Chem. Int. Ed. 2013, 52, 3272
21. Z. Xu, Q. Wang, J. Zhu, J. Am. Chem. Soc. 2013, 135, 19127
22. W. Ren, Q. Wang, J. Zhu, Angew. Chem. 2014, 126, 1849
23. Angew. Chem. Int. Ed. 2014, 53, 1818.
24. T. Akiyama, J. Itoh, K. Yokota, K. Fuchibe, Angew. Chem. 2004, 116, 1592
25. Angew. Chem. Int. Ed. 2004, 43, 1566
26. D. Uraguchi, K. Sorimatchi, M. Terada, J. Am. Chem. Soc. 2004, 126, 11804.
27. T. Akiyama, Chem. Rev. 2007, 107, 5744
28. M. Terada, Chem. Commun. 2008, 4097
29. D. Kampen, C. M. Reisinger, B. List, Top. Curr. Chem. 2010, 291, 395
30. M. Terada, Curr. Org. Chem. 2011, 15, 2227
31. M. Rueping, A. Kuenkel, I. Atodiresei, Chem. Soc. Rev. 2011, 40, 4539
32. C. Zheng, S.-L. You, Chem. Soc. Rev. 2012, 41, 2498.
33. E. García-Urdiales, I. Alfonso, V. Gotor, Chem. Rev. 2005, 105, 313.
34. Y. Chen, P. McDavid, L. Deng, Chem. Rev. 2003, 103, 2965
35. L. Atodiresei, I. Schiffers, C. Bolm, Chem. Rev. 2007, 107, 5683.
36. Chiral phosphoric acid-catalyzed desymmetrization, see
37. S. Xu, Z. Wang, X. Zhang, X. Zhang, K. Ding, Angew. Chem. 2008, 120, 2882
38. Angew. Chem. Int. Ed. 2008, 47, 2840
39. E. B. Rowland, G. B. Rowland, E. Rivera-Otero, J. C. Antilla, J. Am. Chem. Soc. 2007, 129, 12084
40. K. Mori, T. Katoh, T. Suzuki, T. Noji, M. Yamanaka, T. Akiyama, Angew. Chem. 2009, 121, 9832
41. Angew. Chem. Int. Ed. 2009, 48, 9652
42. Q.-W. Zhang, C.-A. Fan, H.-J. Zhang, Y.-Q. Tu, Y.-M. Zhao, P. Gu, Z.-M. Chen, Angew. Chem. 2009, 121, 8724
43. Angew. Chem. Int. Ed. 2009, 48, 8572
44. G. D. Sala, A. Lattanzi, Org. Lett. 2009, 11, 3330
45. V. N. Wakchaure, B. List, Angew. Chem. 2010, 122, 4230
46. Angew. Chem. Int. Ed. 2010, 49, 4136
47. Q. Gu, Z.-Q. Rong, C. Zheng, S.-L. You, J. Am. Chem. Soc. 2010, 132, 4056
48. L. Ren, T. Lei, L.-Z. Gong, Chem. Commun. 2011, 47, 11683
49. S. Müller, M. J. Webber, B. List, J. Am. Chem. Soc. 2011, 133, 18534
50. M. Yang, Y.-M. Zhao, S.-Y. Zhang, Y.-Q. Tu, F.-M. Zhang, Chem. Asian J. 2011, 6, 1344
51. D. M. Rubush, M. A. Morges, B. J. Rose, D. H. Thamm, T. Rovis, J. Am. Chem. Soc. 2012, 134, 13554
52. K. Mori, Y. Ichikawa, M. Kobayashi, Y. Shibata, M. Yamanaka, T. Akiyama, J. Am. Chem. Soc. 2013, 135, 3964
53. Z. Wang, Z. Chen, J. Sun, Angew. Chem. 2013, 125, 6817
54. Angew. Chem. Int. Ed. 2013, 52, 6685
55. Z. Chen, J. Sun, Angew. Chem. 2013, 125, 13838
56. Angew. Chem. Int. Ed. 2013, 52, 13593
57. G. Qabaja, J. E. Wilent, A. R. Benavides, G. E. Bullard, K. S. Petersen, Org. Lett. 2013, 15, 1266
58. A. D. Lackner, A. V. Samant, F. D. Toste, J. Am. Chem. Soc. 2013, 135, 14090; metal/phosphoric acid catalyzed desymmetrization
59. Z. Chai, T. J. Rainey, J. Am. Chem. Soc. 2012, 134, 3615
60. B. Guo, G. Schwarzwalder, J. T. Njardarson, Angew. Chem. 2012, 124, 5773
61. Angew. Chem. Int. Ed. 2012, 51, 5675
62. A. K. Mourad, J. Leutzow, C. Czekelius, Angew. Chem. 2012, 124, 11311
63. Angew. Chem. Int. Ed. 2012, 51, 11149.
64. For other recent examples of chiral phosphoric acid catalyzed kinetic resolution/dynamic kinetic resolution, see
65. F.-L. Sun, X.-J. Zheng, Q. Gu, Q.-L. He, S.-L. You, Eur. J. Org. Chem. 2010, 47
66. M. Rueping, U. Uria, M.-Y. Lin, I. Atodiresei, J. Am. Chem. Soc. 2011, 133, 3732
67. C. Wang, H.-W. Luo, L.-Z. Gong, Synlett 2011, 992
68. G. Lu, V. B. Birman, Org. Lett. 2011, 13, 356
69. M. Yamanaka, M. Hoshino, T. Katoh, K. Mori, T. Akiyama, Eur. J. Org. Chem. 2012, 4508
70. X.-S. Wu, S.-K. Tian, Chem. Commun. 2012, 48, 898
71. I. Čoric̈, J. H. Kim, T. Vlaar, M. Patil, W. Thiel, B. List, Angew. Chem. 2013, 125, 3574
72. Angew. Chem. Int. Ed. 2013, 52, 3490
73. S. Harada, S. Kuwano, Y. Yamaoka, K.-I. Yamada, K. Takasu, Angew. Chem. 2013, 125, 10417
74. Angew. Chem. Int. Ed. 2013, 52, 10227
75. K. Saito, Y. Shibata, M. Yamanaka, T. Akiyama, J. Am. Chem. Soc. 2013, 135, 11740; silver phosphate catalyzed
76. Y. Wang, K. Zheng, R. Hong, J. Am. Chem. Soc. 2012, 134, 4096.
77. R. Chong, P. S. Clezy, Aust. J. Chem. 1967, 20, 123.
78. CCDC 1002333 (12 a) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.
79. The structure of the bislactone 12 a in the solid state did not possess an obvious plane of symmetry. However, we use the term desymmetrization in this paper for the sake of convenience.
80. I. Čoric̈, B. List, Nature 2012, 483, 315
81. S. Liao, I. Čoric̈, Q. Wang, B. List, J. Am. Chem. Soc. 2012, 134, 10765
82. J. H. Kim, I. Čoric̈, S. Vellalath, B. List, Angew. Chem. 2013, 125, 4570
83. Angew. Chem. Int. Ed. 2013, 52, 4474.
84. I. Čoric̈, S. Müller, B. List, J. Am. Chem. Soc. 2010, 132, 17370
85. F. Xu, D. Huang, C. Han, W. Shen, X. Lin, Y. Wang, J. Org. Chem. 2010, 75, 8677.
86. The quality of the monocrystal was not good enough to create a cif file. However, the so generated structure (see the Supporting Information) allowed us to determine without ambiguity the absolute configuration of 2 a.
87. Isolation
88. D. J. Abraham, R. D. Rosenstein, R. L. Lyon, H. H. S. Fong, Tetrahedron Lett. 1972, 13, 909
89. K. T. De Silva, A. H. Ratcliffe, G. F. Smith, G. N. Smith, Tetrahedron Lett. 1972, 13, 913
90. for a review, see:, O. Baudoin, D. Guénard, F. Guéritte, Mini-rev. Org. Chem. 2004, 1, 333.
91. For total synthesis of (±)-rhazinilam, see
92. A. H. Ratcliffe, G. F. Smith, G. N. Smith, Tetrahedron Lett. 1973, 14, 5179
93. J. A. Johnson, D. Sames, J. Am. Chem. Soc. 2000, 122, 6321
94. P. Magnus, T. Rainey, Tetrahedron 2001, 57, 8647
95. A. L. Bowie, Jr., C. C. Hughes, D. Trauner, Org. Lett. 2005, 7, 5207
96. L. McMurray, E. M. Beck, M. J. Gaunt, Angew. Chem. 2012, 124, 9422
97. Angew. Chem. Int. Ed. 2012, 51, 9288
98. X. Sui, R. Zhu, G. Li, X, Ma, Z. Gu, J. Am. Chem. Soc. 2013, 135, 9318; for synthesis of (-)-rhazinilam, see
99. J. A. Johnson, N. Li, D. Sames, J. Am. Chem. Soc. 2002, 124, 6900
100. Z. Liu, A. S. Wasmuth, S. G. Nelson, J. Am. Chem. Soc. 2006, 128, 10352
101. M. G. Banwell, D. A. S. Beck, A. C. Willis, ARKIVOC 2006, 163
102. Z. Gu, A. Zakarian, Org. Lett. 2010, 12, 4224
103. K. Sugimoto, K. Toyoshima, S. Nonaka, K. Kotaki, H. Ueda, H. Tokuyama, Angew. Chem. 2013, 125, 7309
104. Angew. Chem. Int. Ed. 2013, 52, 7168.
105. M. Motegi, A. E. Nugroho, Y. Hirasawa, T. Arai, A. H. A. Hadi, H. Morita, Tetrahedron Lett. 2012, 53, 1227.
106. Y.-C. Wu, J. Zhu, J. Org. Chem. 2008, 73, 9522.
107. K. C. Nicolaou, C. J. N. Mathison, T. Montagnon, Angew. Chem. 2003, 115, 4211
108. Angew. Chem. Int. Ed. 2003, 42, 4077.
109. R. Grigg, P. Myers, A. Somasunderam, V. Sridharan, Tetrahedron 1992, 48, 9735.
110. K. C. Nicolaou, A. A. Estrada, G. C. Freestone, S. H. Lee, X. Alvarez-Mico, Tetrahedron 2007, 63, 6088.
111. Purification by semipreparative SFC on a chiral OD-H column afforded enantiopure leucomidine B.