Total Synthesis of Atisane-Type Diterpenoids: Application of Diels-Alder Cycloadditions of Podocarpane-Type Unmasked ortho-Benzoquinones

Journal of the American Chemical Society

Volumn 137, Issue 42, 2015, Pages 13706-13714

  Song, Liqiang ^a   Zhu, Guili ^a   Liu, Yongjiang ^a   Liu, Bo ^a,b   Qin, Song ^a  

^a China   (China)

^b CHINA PHARMACEUTICAL UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; CYCLIZATION; CYCLOADDITION; LIPIDS; MANGANESE; MUSCULOSKELETAL SYSTEM;

BICYCLO[2.2.2]OCTANE; CASCADE CYCLIZATION; COMPLEX MOLECULES; DIELS-ALDER CYCLOADDITIONS; NATURAL PRODUCTS; SYNTHETIC UTILITY; TOTAL SYNTHESIS; [4 + 2] CYCLOADDITION;

SYNTHESIS (CHEMICAL);

BENZOQUINONE DERIVATIVE; DITERPENOID;

ARTICLE; CHEMICAL STRUCTURE; CONFORMATION; CRYSTALLIZATION; CYCLIZATION; CYCLOADDITION; DESILYLATION; DIASTEREOISOMER; DIELS ALDER REACTION; EPOXIDATION; GEOMETRY; HYDROXYLATION; NUCLEAR OVERHAUSER EFFECT; SCREENING TEST; STEREOCHEMISTRY; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 84946021794     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/jacs.5b08958     Document Type: Article

References (114)

1. Zhou, B.; Li, X.; Tang, H.; Miao, Z.; Feng, H.; Li, Y. Org. Biomol. Chem. 2011, 9, 3176 10.1039/c0ob01239d
2. Cambie, R. C.; Rutledge, P. S.; Stevenson, R. J.; Woodgate, P. D. J. Organomet. Chem. 1995, 486, 199 10.1016/0022-328X(94)05039-E
3. Matsumoto, T.; Imai, S.; Mimura, K.; Aiba, K. Chem. Lett. 1988, 17, 1399 10.1246/cl.1988.1399
4. Dickschat, J. S. Nat. Prod. Rep. 2011, 28, 1917 10.1039/c1np00063b
5. Dewick, P. M. Nat. Prod. Rep. 2002, 19, 181 10.1039/b002685i
6. Gao, W.; Hillwig, M. L.; Huang, L.; Cui, G.; Wang, X.; Kong, J.; Yang, B.; Peters, R. J. Org. Lett. 2009, 11, 5170 10.1021/ol902051v
7. Tantillo, D. J. Nat. Prod. Rep. 2011, 28, 1035 10.1039/c1np00006c
8. Tantillo, D. J. Chem. Soc. Rev. 2010, 39, 2847 10.1039/b917107j
9. Hong, Y. J.; Tantillo, D. J. Nat. Chem. 2014, 6, 104 10.1038/nchem.1843
10. Hong, Y. J.; Tantillo, D. J. Chem. Sci. 2013, 4, 2512 10.1039/c3sc50571e
11. Hong, Y. J.; Tantillo, D. J. J. Am. Chem. Soc. 2010, 132, 5375 10.1021/ja9084786
12. Wang, F.-P.; Liang, X.-T. In The Alkaloids: Chemistry and Biology; Cordell, G. A., Ed.; Elsevier Science: New York, 2002; Vol. 59, pp 1-280.
13. Wang, F.-P.; Chen, Q.-H.; Liu, X.-Y. Nat. Prod. Rep. 2010, 27, 529 10.1039/b916679c
14. Wang, F.-P.; Chen, Q.-H.; Liang, X.-T. In The Alkaloids: Chemistry and Biology; Cordell, G. A., Ed.; Elsevier Science: New York, 2009; Vol. 67, pp 1-78.
15. Wang, F.-P.; Chen, Q.-H. In The Alkaloids: Chemistry and Biology; Cordell, G. A., Ed.; Elsevier Science: New York, 2010; Vol. 69, pp 1-577.
16. Johnston, J. P.; Overton, K. H. J. Chem. Soc., Perkin Trans. 1 1972, 1490 10.1039/p19720001490
17. Johnston, J. P.; Overton, K. H. J. Chem. Soc. Chem. Commun. 1969, 329
18. Zhu, G.; Liu, R.; Liu, B. Synthesis 2015, 47, 2691 10.1055/s-0034-1378743
19. Hamlin, A. M.; Kisunzu, J. K.; Sarpong, R. Org. Biomol. Chem. 2014, 12, 1846 10.1039/c3ob42541j
20. Cherney, C. C.; Baran, P. S. Isr. J. Chem. 2011, 51, 391 10.1002/ijch.201100005
21. Cherney, E. C.; Green, J. C.; Baran, P. S. Angew. Chem., Int. Ed. 2013, 52, 9019 10.1002/anie.201304609
22. Hamin, A. M.; Cortez, F. J.; Lapointe, D.; Sarpong, R. Angew. Chem., Int. Ed. 2013, 52, 4854 10.1002/anie.201209030
23. Hamlin, A. M.; Lapointe, D.; Owens, K.; Sarpong, R. J. Org. Chem. 2014, 79, 6783 10.1021/jo501214b
24. Ihara, M.; Suzuki, M.; Fukumoto, K.; Kametani, T.; Kabuto, C. J. Am. Chem. Soc. 1988, 110, 1963 10.1021/ja00214a050
25. Ihara, M.; Suzuki, M.; Fukumoto, K.; Kametani, T.; Kabuto, C. J. Am. Chem. Soc. 1990, 112, 1164 10.1021/ja00159a042
26. Guthrie, R. W.; Valenta, Z.; Wiesner, K. Tetrahedron Lett. 1966, 7, 4645 10.1016/S0040-4039(00)70092-X
27. Nagata, W.; Sugasawa, T.; Narisada, M.; Wakabayashi, T.; Hayase, Y. J. Am. Chem. Soc. 1963, 85, 2342 10.1021/ja00898a048
28. Muratake, H.; Natsume, M.; Nakai, H. Tetrahedron 2006, 62, 7093 10.1016/j.tet.2006.04.086
29. Toyota, M.; Wada, T.; Ihara, M. Org. Lett. 1999, 1, 1627 10.1021/ol990264u
30. Toyota, M.; Wada, T.; Fukumoto, K.; Ihara, M. J. Am. Chem. Soc. 1998, 120, 4916 10.1021/ja9739042
31. Toyota, M.; Wada, T.; Ihara, M. J. Org. Chem. 2000, 65, 4565 10.1021/jo000142b
32. Toyota, M.; Asano, T.; Ihara, M. Org. Lett. 2005, 7, 3929 10.1021/ol051411t
33. Abad, A.; Agulló, C.; Cuñat, A. C.; Navarro, I. Tetrahedron Lett. 2001, 42, 8965 10.1016/S0040-4039(01)01953-0
34. Abad, A.; Agulló, C.; Cuñat, A. C.; Navarro, I.; de Arellano, M. C. R. Synlett 2001, 349
35. Abad, A.; Agulló, C.; Cuñat, A. C.; de Alfonso Marzal, I.; Navarro, I.; Gris, A. Tetrahedron 2006, 62, 3266 10.1016/j.tet.2006.01.062
36. Abad, A.; Agulló, C.; Cuñat, A. C.; de Alfonso Marzal, I.; Gris, A.; Navarro, I.; de Arellano, C. R. Tetrahedron 2007, 63, 1664 10.1016/j.tet.2006.11.083
37. Ungur, N.; Kulciţki, V.; Chetraru, O.; Grinco, M.; Vlad, P. F. Helv. Chim. Acta 2013, 96, 864 10.1002/hlca.201200305
38. Cherney, E. C.; Lopchuk, J. M.; Green, J. C.; Baran, P. S. J. Am. Chem. Soc. 2014, 136, 12592 10.1021/ja507321j
39. Peese, K. M.; Gin, D. Y. J. Am. Chem. Soc. 2006, 128, 8734 10.1021/ja0625430
40. Peese, K. M.; Gin, D. Y. Chem.-Eur. J. 2008, 14, 1654 10.1002/chem.200701290
41. Liu, X.-Y.; Cheng, H.; Li, X.-H.; Chen, Q.-H.; Xu, L.; Wang, F.-P. Org. Biomol. Chem. 2012, 10, 1411 10.1039/C1OB06704D
42. Singh, V.; Bhalerao, P.; Sahu, B. C.; Mobin, S. M. Tetrahedron 2013, 69, 137 10.1016/j.tet.2012.10.051
43. Nishiyama, Y.; Han-ya, Y.; Yokoshima, S.; Fukuyama, T. J. Am. Chem. Soc. 2014, 136, 6598 10.1021/ja503023h
44. Rakotonandrasana, O. L.; Raharinjato, F. H.; Rajaonarivelo, M.; Dumontet, V.; Martin, M.-T.; Bignon, J.; Rasoanaivo, P. J. Nat. Prod. 2010, 73, 1730 10.1021/np1005086
45. Liu, J.-H.; Latif, A.; Ali, M.; Zhang, G.-P.; Xiang, W.-J.; Ma, L.; Arfan, M.; Hu, L.-H. Phytochemistry 2012, 75, 153 10.1016/j.phytochem.2011.11.016
46. Li, Y.; Liu, J.; Yu, S.; Proksch, P.; Gu, J.; Lin, W. Phytochemistry 2010, 71, 2124 10.1016/j.phytochem.2010.08.011
47. Wang, Z. C.; Lin, Y. M.; Feng, D. Q.; Ke, C. H.; Lin, P.; Yan, C. L.; Chen, J. D. Molecules 2009, 14, 414 10.3390/molecules14010414
48. Wang, J.-D.; Li, Z.-Y.; Xiang, W.-S.; Guo, Y.-W. Helv. Chim. Acta 2006, 89, 1367 10.1002/hlca.200690136
49. Wang, J.-D.; Li, Z.-Y.; Guo, Y.-W. Helv. Chim. Acta 2005, 88, 979 10.1002/hlca.200590092
50. Lal, A. R.; Cambie, R. C.; Rutledge, P. S.; Woodgate, P. D. Phytochemistry 1990, 29, 1925 10.1016/0031-9422(90)85042-E
51. Breitler, S.; Carreira, E. M. Angew. Chem., Int. Ed. 2013, 52, 11168 10.1002/anie.201305822
52. Guo, Y.; Liu, Q.; Jia, Y. Chem. Commun. 2015, 51, 889 10.1039/C3CC48897G
53. Behera, T. K.; Singh, V. Tetrahedron 2014, 70, 7983 10.1016/j.tet.2014.08.044
54. Ushakov, D. B.; Maier, M. E. Synlett 2013, 24, 705 10.1055/s-0032-1318366
55. Schmitz, F. J.; Vanderah, D. J.; Hollenbeak, K. H.; Enwall, C. E. L.; Gopichand, Y. J. Org. Chem. 1983, 48, 3941 10.1021/jo00170a011
56. Cafieri, F.; Fattorusso, E.; Mahajnah, Y.; Mangoni, A. Magn. Reson. Chem. 1995, 33, 286 10.1002/mrc.1260330411
57. Satti, N. K.; Suri, O. P.; Dhar, K. L. J. Nat. Prod. 1987, 50, 790 10.1021/np50053a003
58. Leisch, H.; Morley, K.; Lau, P. C. K. Chem. Rev. 2011, 111, 4165 10.1021/cr1003437
59. Alphand, V.; Wohlgemuth, R. Curr. Org. Chem. 2010, 14, 1928 10.2174/138527210792927519
60. Wang, Y.; Lim, L.; Madilao, L.; Lah, L.; Bohlmann, J.; Breuil, C. Appl. Environ. Microbiol. 2014, 80, 4566 10.1128/AEM.00670-14
61. Cernuchova, P.; Mihovilovic, M. D. Org. Biomol. Chem. 2007, 5, 1715 10.1039/b703175k
62. Van der Werf, M. J. Biochem. J. 2000, 347, 693 10.1042/0264-6021:3470693
63. Matsuda, Y.; Wakimoto, T.; Mori, T.; Awakawa, T.; Abe, I. J. Am. Chem. Soc. 2014, 136, 15326 10.1021/ja508127q
64. Matsuda, Y.; Awakawa, T.; Wakimoto, T.; Abe, I. J. Am. Chem. Soc. 2013, 135, 10962 10.1021/ja405518u
65. For insightful study on catalytic mechanism of BVMO, see: Yachnin, B. J.; Sprules, T.; McEvoy, M. B.; Lau, P. C. K.; Berghuis, A. M. J. Am. Chem. Soc. 2012, 134, 7788 10.1021/ja211876p
66. Van der Vlugt-Bergmans, C. J. B.; Van der Werf, M. J. Appl. Environ. Microbiol. 2001, 67, 733 10.1128/AEM.67.2.733-741.2001
67. Van der Werf, M. J.; Boot, A. M. Microbiology 2000, 146, 1129 10.1099/00221287-146-5-1129
68. Liu, C.; Tagami, K.; Minami, A.; Matsumoto, T.; Frisvad, J. C.; Suzuki, H.; Ishikawa, J.; Gomi, K.; Oikawa, H. Angew. Chem., Int. Ed. 2015, 54, 5748 10.1002/anie.201501072
69. Citron, C. A.; Brock, N. L.; Tudzynsk, B.; Dickschat, J. S. Chem. Commun. 2014, 50, 5224 10.1039/C3CC45982A
70. Suri, O. P.; Satti, N. K.; Suri, K. A.; Dhar, K. L.; Kachroo, P. L.; Kawasaki, T.; Miyahara, K.; Tsunehiro, T.; Fumiko, Y. J. Nat. Prod. 1990, 53, 470 10.1021/np50068a030
71. Lichter, P. A.; Milller, S. J. Nat. Chem. 2012, 4, 990 10.1038/nchem.1469
72. Xu, S.; Gu, J.; Li, H.; Ma, D.; Xie, X.; She, X. Org. Lett. 2014, 16, 1996 10.1021/ol500553x
73. Topczewski, J. J.; Kodet, J. G. J. Org. Chem. 2011, 76, 909 10.1021/jo1022102
74. Yu, L.-G.; Ni, T.-F.; Gao, W.; He, Y.; Wang, Y.-Y.; Cui, H.-W.; Yang, C.-G.; Qiu, W.-W. Eur. J. Med. Chem. 2015, 90, 10 10.1016/j.ejmech.2014.11.015
75. Onyango, E. O.; Fu, L.; Gribble, G. W. Org. Lett. 2014, 16, 322 10.1021/ol403289y
76. Kim, M. B.; Shaw, J. T. Org. Lett. 2010, 12, 3324 10.1021/ol100929z
77. Zhao, J.-F.; Zhao, Y.-J.; Loh, T.-P. Chem. Commun. 2008, 1353 10.1039/b718337b
78. Roche, S. P.; Porco, J. A., Jr. Angew. Chem., Int. Ed. 2011, 50, 4068 10.1002/anie.201006017
79. Liao, C.-C. Pure Appl. Chem. 2005, 77, 1221 10.1351/pac200577071221
80. Nair, V.; Menon, R. S.; Biju, A. T.; Abhilash, K. G. Chem. Soc. Rev. 2012, 41, 1050 10.1039/C1CS15186J
81. Kumar, V.; Ramanathan, S.; Sang, D.; Chen, X.; Lemal, D. M. J. Org. Chem. 2012, 77, 966 10.1021/jo202193c
82. Thomas, A.; Anilkumar, G.; Nair, V. Tetrahedron 1996, 52, 2481 10.1016/0040-4020(95)01069-6
83. Nair, V.; Maliakal, D. Res. Chem. Intermed. 2002, 28, 337 10.1163/15685670260188647
84. Kaicharia, T.; Bhojgude, S. S.; Biju, A. Org. Lett. 2012, 14, 6238 10.1021/ol302997q
85. Nair, V.; Maliakal, D.; Treesa, P. M.; Rath, N. P.; Eigendorf, G. K. Synthesis 2000, 2000, 850 10.1055/s-2000-6285
86. Müller, G. H.; Lang, A.; Seithel, D. R.; Waldmann, H. Chem.-Eur. J. 1998, 4, 2513 10.1002/(SICI)1521-3765(19981204)4:12<2513::AID-CHEM2513>3.0.CO;2-4
87. Nair, V.; Kumar, S. Synlett 1996, 1996, 1143 10.1055/s-1996-5699
88. Liao, C. C.; Lin, H. S. J. Chin. Chem. Soc. 1986, 33, 73 10.1002/jccs.198600009
89. See Supporting Information for details on DFT calculation.
90. Hong, Y. J.; Tantillo, D. J. Chem. Sci. 2013, 4, 2512 10.1039/c3sc50571e
91. Shibasaki, K.; Fujii, A.; Mikami, N.; Tsuzuki, S. J. Phys. Chem. A 2006, 110, 4397 10.1021/jp0605909
92. Ugozzoli, F.; Arduini, A.; Massera, C.; Pochini, A.; Secchi, A. New J. Chem. 2002, 26, 1718 10.1039/b208432e
93. Mo, Y.; Subramanian, G.; Gao, J.; Ferguson, D. M. J. Am. Chem. Soc. 2002, 124, 4832 10.1021/ja0174433
94. Nawrat, C. C.; Moody, C. J. Angew. Chem., Int. Ed. 2014, 53, 2056 10.1002/anie.201305908
95. Parvatkar, P. T.; Kadam, H. K.; Tilve, S. G. Tetrahedron 2014, 70, 2857 10.1016/j.tet.2014.02.048
96. Wan, C. Y.; Deng, J.; Liu, H.; Bian, M.; Li, A. Sci. China: Chem. 2014, 57, 926 10.1007/s11426-014-5144-5
97. Yuan, C.; Du, B.; Yang, L.; Liu, B. J. Am. Chem. Soc. 2013, 135, 9291 10.1021/ja4040335
98. Du, B.; Yuan, C.; Yu, T.; Yang, L.; Liu, B.; Qin, S. Chem.-Eur. J. 2014, 20, 2613 10.1002/chem.201304378
99. Yang, L.; Yue, G.; Yuan, C.; Du, B.; Deng, H.; Liu, B. Synlett 2014, 25, 2471 10.1055/s-0034-1379001
100. Inoki, S.; Kato, K.; Isayama, S.; Mukaiyama, T. Chem. Lett. 1990, 1869 10.1246/cl.1990.1869
101. Kato, K.; Yamada, T.; Takai, T.; Inoki, S.; Isayama, S. Bull. Chem. Soc. Jpn. 1990, 63, 179 10.1246/bcsj.63.179
102. Inoki, S.; Kato, K.; Takai, T.; Isayama, S.; Yamada, T.; Mukaiyama, T. Chem. Lett. 1989, 515 10.1246/cl.1989.515
103. Hao, X. Huaxue Jinzhan 2009, 21, 84
104. Kume, T.; Katuski, H.; Akaike, A. Biol. Pharm. Bull. 2004, 27, 964 10.1248/bpb.27.964
105. Hao, X.; Shen, Y.; Li, L.; He, H. Curr. Med. Chem. 2003, 10, 2253 10.2174/0929867033456684
106. Kume, T.; Asai, N.; Nishikawa, H.; Mano, N.; Terauchi, T.; Taguchi, R.; Shirakawa, H.; Osakada, F.; Mori, H.; Asakawa, N.; Yonaga, M.; Nishizawa, Y.; Sugimoto, H.; Shimohama, S.; Katsuki, H.; Kaneko, S.; Akaike, A. Proc. Natl. Acad. Sci. U. S. A. 2002, 99, 3288 10.1073/pnas.052693999
107. Rafferty, R. J.; Hicklin, R. W.; Maloof, K. A.; Hergenrother, P. J. Angew. Chem., Int. Ed. 2014, 53, 220 10.1002/anie.201308743
108. Huigens, R. W., III; Morrison, K. C.; Hicklin, R. W.; Flood, T. A., Jr; Richter, M. F.; Hergenrother, P. J. Nat. Chem. 2013, 5, 195 10.1038/nchem.1549
109. Fuentes, R. G.; Toume, K.; Arai, M. A.; Sadhu, S. K.; Ahmed, F.; Ishibashi, M. J. Nat. Prod. 2015, 78, 864 10.1021/np500933v
110. Munoz, M. A.; Chamy, C.; Bucio, M. A.; Hernandez-Baragan, A.; Joseph-Nathan, P. Tetrahedron Lett. 2014, 55, 4274 10.1016/j.tetlet.2014.06.004
111. Liu, Q.; Yang, Q.-M.; Hu, H.-J.; Yang, L.; Yang, Y.-B.; Chou, G.-X.; Wang, Z.-T. J. Nat. Prod. 2014, 77, 1594 10.1021/np500150f
112. Ahsan, M.; Islam, SK. N.; Gray, A. I.; Stimson, W. H. J. Nat. Prod. 2003, 66, 958 10.1021/np020356j
113. Matsuda, Y.; Wakimoto, T.; Mori, T.; Awakawa, T.; Abe, I. J. Am. Chem. Soc. 2014, 136, 15326 10.1021/ja508127q
114. Dunn, A. W.; Johnstone, R. A. W.; Sklarz, B. J. Chem. Soc., Chem. Commun. 1978, 533 10.1039/c39780000533