Total synthesis and structural revision of (+)-uprolide G acetate

Angewandte Chemie - International Edition

Volumn 54, Issue 2, 2015, Pages 627-632

  Zhu, Liangyu ^a   Liu, Yuan ^a   Ma, Renze ^a   Tong, Rongbiao ^a  

^a HONG KONG UNIVERSITY OF SCIENCE AND TECHNOLOGY   (Hong Kong)

Author keywords

Macrocycles; Natural products; Rearrangements; Structure elucidation; Total synthesis

Indexed keywords

SYNTHESIS (CHEMICAL); VOLATILE FATTY ACIDS;

MACROCYCLES; NATURAL PRODUCTS; REARRANGEMENTS; STRUCTURE ELUCIDATION; TOTAL SYNTHESIS;

CYCLIZATION;

BRIDGED COMPOUND; LACTONE; UPROLIDE G;

CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SYNTHESIS; X RAY DIFFRACTION;

BRIDGED COMPOUNDS; CYCLIZATION; LACTONES; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; X-RAY DIFFRACTION;

EID: 84922769275     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201409618     Document Type: Article

References (103)

1. J. C. Coll, Chem. Rev. 1992, 92, 613-631.
2. a) J. W. Blunt, B. R. Copp, R. A. Keyzers, M. H. G. Munro, M. R. Prinsep, Nat. Prod. Rep. 2014, 31, 160-258;
3. b) J. W. Blunt, B. R. Copp, R. A. Keyzers, M. H. G. Munro, M. R. Prinsep, Nat. Prod. Rep. 2013, 30, 237-323;
4. c) J. W. Blunt, B. R. Copp, R. A. Keyzers, M. H. G. Munro, M. R. Prinsep, Nat. Prod. Rep. 2012, 29, 144-222;
5. d) J. W. Blunt, B. R. Copp, R. A. Keyzers, M. H. G. Munro, M. R. Prinsep, Nat. Prod. Rep. 2011, 28, 196-268;
6. e) D. J. Faulkner, Nat. Prod. Rep. 2002, 19, 1-49;
7. f) D. J. Faulkner, Nat. Prod. Rep. 2001, 18, 1R-49R;
8. g) D. J. Faulkner, Nat. Prod. Rep. 2000, 17, 7-55.
9. a) G. Li, Y. Zhang, Z. Deng, L. van Ofwegen, P. Proksch, W. Lin, J. Nat. Prod. 2005, 68, 649-652;
10. b) W. Zhang, K. Krohn, J. Ding, Z.-H. Miao, X.-H. Zhou, S.-H. Chen, G. Pescitelli, P. Salvadori, T. Kurtan, Y.-W. Guo, J. Nat. Prod. 2008, 71, 961-966.
11. a) H.-C. Huang, A. F. Ahmed, J.-H. Su, C.-H. Chao, Y.-C. Wu, M. Y. Chiang, J.-H. Sheu, J. Nat. Prod. 2006, 69, 1554-1559;
12. b) H.-C. Huang, C.-H. Chao, Y.-H. Kuo, J.-H. Sheu, Chem. Biodiversity 2009, 6, 1232-1242;
13. c) G.-H. Wang, H.-C. Huang, J.-H. Su, C.-Y. Huang, C.-H. Hsu, Y.-H. Kuo, J.-H. Sheu, Bioorg. Med. Chem. Lett. 2011, 21, 7201-7204;
14. d) C.-Y. Duh, S.-K. Wang, B.-T. Huang, C.-F. Dai, J. Nat. Prod. 2000, 63, 884-885.
15. a) L.-T. Wang, S.-K. Wang, K. Soong, C.-Y. Duh, Chem. Pharm. Bull. 2007, 55, 766-770;
16. b) S.-K. Wang, C.-Y. Duh, Mar. Drugs 2012, 10, 306-318.
17. a) S. E. Ealick, D. Van der Helm, A. J. Weinheimer, Acta Crystallogr. Sect. B 1975, 31, 1618-1626;
18. b) D. Van der Helm, S. E. Ealick, A. J. Weinheimer, Cryst. Struct. Commun. 1974, 3, 167-171;
19. c) L. A. Fontán, W. Y. Yoshida, A. D. Rodríguez, J. Org. Chem. 1990, 55, 4956-4960;
20. d) A. Iwamaru, E. Iwado, S. Kondo, R. A. Newman, B. Vera, A. D. Rodríguez, Y. Kondo, Mol. Cancer Ther. 2007, 6, 184-192.
21. a) A. D. Rodríguez, I. C. Piña, J. J. Soto, D. R. Rojas, C. L. Barnes, Can. J. Chem. 1995, 73, 643-654;
22. b) A. D. Rodríguez, J. J. Soto, I. C. Pina, J. Nat. Prod. 1995, 58, 1209-1216;
23. c) A. D. Rodríguez, A. L. Acosta, J. Nat. Prod. 1998, 61, 40-45;
24. d) Y.-P. Shi, A. D. Rodríguez, C. L. Barnes, J. A. Sánchez, R. G. Raptis, P. Baran, J. Nat. Prod. 2002, 65, 1232-1241.
25. R. R. Kitson, A. Millemaggi, R. J. K. Taylor, Angew. Chem. Int. Ed. 2009, 48, 9426-9451;
26. Angew. Chem. 2009, 121, 9590-9615.
27. a) B. B. Patel, T. G. Waddell, R. M. Pagni, Fitoterapia 2001, 72, 511-515;
28. b) H. N. Pati, U. Das, R. K. Sharma, J. R. Dimmock, Mini-Rev. Med. Chem. 2007, 7, 131-139;
29. c) Y. Higuchi, F. Shimoma, M. Ando, J. Nat. Prod. 2003, 66, 810-817;
30. d) E. Rodriguez, G. H. N. Towers, J. C. Mitchell, Phytochemistry 1976, 15, 1573-1580.
31. A. D. Rodríguez, I. C. Piña, C. L. Barnes, J. Org. Chem. 1995, 60, 8096-8100.
32. A. D. Rodríguez, J. J. Soto, C. L. Barnes, J. Org. Chem. 2000, 65, 7700-7702.
33. a) J. Li, J. S. Cisar, C.-Y. Zhou, B. Vera, H. Williams, A. D. Rodríguez, B. F. Cravatt, D. Romo, Nat. Chem. 2013, 5, 510-517;
34. b) A. D. Rodríguez, I. C. Piña, A. L. Acosta, C. Ramírez, J. J. Soto, J. Org. Chem. 2001, 66, 648-658;
35. c) M. A. Tius, Chem. Rev. 1988, 88, 719-732;
36. d) J. A. Marshall, S. L. Crooks, B. S. DeHoff, J. Org. Chem. 1988, 53, 1616-1623;
37. e) D. F. Taber, Y. Song, J. Org. Chem. 1997, 62, 6603-6607.
38. J. A. Marshall, C. A. Griot, H. R. Chobanian, W. H. Myers, Org. Lett. 2010, 12, 4328-4331.
39. a) O. Achmatowicz, Jr., P. Bukowski, B. Szechner, Z. Zwierzchowska, A. Zamojski, Tetrahedron 1971, 27, 1973-1996;
40. b) K. C. Nicolaou, T. M. Baker, T. Nakamura, J. Am. Chem. Soc. 2011, 133, 220-226;
41. c) K. L. Jackson, J. A. Henderson, H. Motoyoshi, A. J. Phillips, Angew. Chem. Int. Ed. 2009, 48, 2346-2350;
42. Angew. Chem. 2009, 121, 2382-2386;
43. d) J. A. Henderson, K. L. Jackson, A. J. Phillips, Org. Lett. 2007, 9, 5299-5302;
44. e) N. D. Griggs, A. J. Phillips, Org. Lett. 2008, 10, 4955-4957;
45. f) B. H. Lipshutz, Chem. Rev. 1986, 86, 795-819;
46. g) J. M. Harris, M. Li, J. G. Scott, G. A. O'Doherty, Strategy and Tactics in Organic Synthesis (Ed. M. Harmata), Elsevier, London, 2004, pp. 221-253;
47. h) Z. Li, T.-F. Leung, R. Tong, Chem. Commun. 2014, 50, 10990-10993;
48. i) J. Ren, R. Tong, J. Org. Chem. 2014, 79, 6987-6995;
49. j) J. Ren, Y. Liu, L. Song, R. Tong, Org. Lett. 2014, 16, 2986-2989.
50. a) C. Harcken, R. Brckner, Angew. Chem. Int. Ed. Engl. 1997, 36, 2750-2752;
51. Angew. Chem. 1997, 109, 2866-2868;
52. b) E. A. Couladouros, A. P. Mihou, Tetrahedron Lett. 1999, 40, 4861-4862;
53. c) M. M. Ahmed, B. P. Berry, T. J. Hunter, D. J. Tomcik, G. A. O'Doherty, Org. Lett. 2005, 7, 745-748;
54. d) P. Y. Hayes, W. Kitching, J. Am. Chem. Soc. 2002, 124, 9718-9719;
55. e) P. Y. Hayes, S. Chow, F. Rahm, P. V. Bernhardt, J. J. De Voss, W. Kitching, J. Org. Chem. 2010, 75, 6489-6501;
56. f) A. L. Hurski, V. N. Zhabinskii, V. A. Khripach, Steroids 2012, 77, 780-790;
57. g) P.-S. Wang, X.-L. Zhou, L.-Z. Gong, Org. Lett. 2014, 16, 976-979.
58. a) R. H. Grubbs, Tetrahedron 2004, 60, 7117-7140;
59. b) R. H. Grubbs, Angew. Chem. Int. Ed. 2006, 45, 3760-3765;
60. Angew. Chem. 2006, 118, 3845-3850.
61. a) A. Gradillas, J. Pérez-Castells, Angew. Chem. Int. Ed. 2006, 45, 6086-6101;
62. Angew. Chem. 2006, 118, 6232-6247;
63. b) A. Fürstner, K. Langemann, Synthesis 1997, 792-803;
64. c) M. Gurjar, S. Nayak, C. V. Ramana, Tetrahedron Lett. 2005, 46, 1881-1884;
65. d) C. V. Ramana, S. R. Salian, M. K. Gurjar, Tetrahedron Lett. 2007, 48, 1013-1016.
66. a) W. S. Johnson, L. Werthemann, W. R. Bartlett, T. J. Brocksom, T. Li, D. J. Faulkner, M. R. Petersen, J. Am. Chem. Soc. 1970, 92, 741-743;
67. b) R. A. Fernandes, A. K. Chowdhury, P. Kattanguru, Eur. J. Org. Chem. 2014, 2833-2871;
68. c) A. M. M. Castro, Chem. Rev. 2004, 104, 2939-3002.
69. A. Abiko, J.-F. Liu, S. Masamune, J. Am. Chem. Soc. 1997, 119, 2586-2587.
70. a) J. A. Bisceglia, L. R. Orelli, Curr. Org. Chem. 2012, 16, 2206-2230;
71. b) B. E. Maryanoff, A. B. Reitz, Chem. Rev. 1989, 89, 863-927.
72. a) S. Hashiguchi, A. Fujii, K. Takehara, T. Ikariya, R. Noyori, J. Am. Chem. Soc. 1995, 117, 7562-7563;
73. b) A. Fujii, S. Hashiguchi, N. Uematsu, T. Ikariya, R. Noyori, J. Am. Chem. Soc. 1996, 118, 2521-2522;
74. c) L. Ferrié, S. Reymond, P. Capdevielle, J. Cossy, Org. Lett. 2007, 9, 2461-2464;
75. d) R. Noyori, S. Hashiguchi, Acc. Chem. Res. 1997, 30, 97-102.
76. a) M. D. Lewis, J. K. Cha, Y. Kishi, J. Am. Chem. Soc. 1982, 104, 4976-4978;
77. b) J. M. Um, K. N. Houk, A. J. Phillips, Org. Lett. 2008, 10, 3769-3772.
78. T. Imamoto, N. Takiyama, K. Nakamura, T. Hatajima, Y. Kamiya, J. Am. Chem. Soc. 1989, 111, 4392-4398.
79. B. W. Gung, Tetrahedron 1996, 52, 5263-5301,
80. A. Mengel, O. Reiser, Chem. Rev. 1999, 99, 1191-1223,
81. a) T. Katsuki, K. B. Sharpless, J. Am. Chem. Soc. 1980, 102, 5974-5976;
82. b) R. M. Hanson, K. B. Sharpless, J. Org. Chem. 1986, 51, 1922-1925.
83. E. Hasegawa, M. Takahashi, T. Horaguchi, Tetrahedron Lett. 1995, 36, 5215-5218.
84. a) E. N. Jacobsen, I. Marko, W. S. Mungall, G. Schroeder, K. B. Sharpless, J. Am. Chem. Soc. 1988, 110, 1968-1970;
85. b) H. C. Kolb, M. S. Van Nieuwenhze, K. B. Sharpless, Chem. Rev. 1994, 94, 2483-2547.
86. T. Janecki, E. Blaszczyk, Tetrahedron Lett. 2001, 42, 2919-2922.
87. a) H. M. R. Hoffmann, J. Rabe, Angew. Chem. Int. Ed. Engl. 1985, 24, 94-110;
88. Angew. Chem. 1985, 97, 96-112;
89. b) P. A. Grieco, Synthesis 1975, 67-82;
90. c) J. C. Sarma, R. P. Sharma, Heterocycles 1986, 24, 441-457;
91. d) N. Petragnani, H. M. C. Ferraz, G. V. J. Silva, Synthesis 1986, 157-183.
92. a) S. Danishefsky, T. Kitahara, R. McKee, P. F. Schuda, J. Am. Chem. Soc. 1976, 98, 6715-6717;
93. b) J. L. Roberts, P. S. Borromeo, C. D. Poulter, Tetrahedron Lett. 1977, 18, 1261-1264.
94. See the Supporting Information.
95. a) "The Chemical Shift": J. B. Lambert, H. F. Shurvell, D. A. Lightner, R. G. Cooks in Organic Structural Spectroscopy, Prentice Hall, Upper Saddle River, New Jersey, 1998, pp. 49-57;
96. b) "Carbon-13 NMR Spectrometry": R. M. Silverstein, F. X. Webster, D. J. Kiemle in Spectrometric Identification of Organic Compounds, 7th ed., Wiley, Hoboken, New Jersey, 2005, pp. 204-229.
97. See Table S1 in the Supporting Information.
98. a) D. A. Evans, S. W. Kaldor, T. K. Jones, J. Clardy, T. J. Stout, J. Am. Chem. Soc. 1990, 112, 7001-7031;
99. b) D. A. Evans, J. A. Gauchet-Prunet, E. M. Carreira, A. B. Charette, J. Org. Chem. 1991, 56, 741-750;
100. c) R. Tirado, J. A. Prieto, J. Org. Chem. 1993, 58, 5666-5673;
101. d) J. Muller, B. Schöllhorn, Angew. Chem. Int. Ed. Engl. 1990, 29, 431-432;
102. Angew. Chem. 1990, 102, 433-435.
103. The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif