Application of Photochemical Rearrangement of Santonin in Total Synthesis of Complex Natural Terpenoids
- Corresponding author: Gao Shuanhu, shgao@chem.ecnu.edu.cn
Citation: Yang Baochao, Gao Shuanhu. Application of Photochemical Rearrangement of Santonin in Total Synthesis of Complex Natural Terpenoids[J]. Acta Chimica Sinica, ;2018, 76(3): 161-167. doi: 10.6023/A17120537
Maimone, T. J.; Baran, P. S. Nat. Chem. Biol. 2007, 3, 396.
doi: 10.1038/nchembio.2007.1
Zhang, D.; Xie, X.; Feng, J. S.; Wen, H. L. Chin. J. Org. Chem. 2016, 36, 202.
(a) Bach, T. ; Hehn, J. P. Angew. Chem. Int. Ed. 2011, 50, 1000. (b) Wan, C. Y. ; Deng, J. ; Liu, H. ; Bian, M. ; Li, A. Sci. China Chem. 2014, 57, 926. Recently Wang et al. achieve the total synthesis of (+)-Chinensiolide B from photochemical rearrangement of santonin, for details see: (c) Zhang, L. Q. ; Dai, X. L. ; Tao, L. Z. ; Xie, C. S. ; Zhang, M. ; Wang, M. Chin. J. Chem. 2017, 35, 1284.
Trommsdorff, H. Ann. Chem. Pharm. 1834, 11, 190.
doi: 10.1002/(ISSN)1099-0690
Barton, D. H. R.; de Mayo, P.; Shafiq, M. J. Chem. Soc. 1957, 929.
For selected examples, see: (a) White, E. H. ; Marx, J. N. J. Am. Chem. Soc. 1967, 89, 5511. (b) Marx, J. N. ; White, E. H. Tetrahedron 1969, 25, 2117. (c) Edgar, M. T. ; Greene, A. E. ; Crabbe, P. J. Org. Chem. 1979, 44, 159. (d) Greene, A. E. J. Am. Chem. Soc. 1980, 102, 5337. (e) Greene, A. E. ; Edgar, M. T. J. Org. Chem. 1989, 54, 1468. (f) Delair, P. ; Kann, N. ; Greene, A. E. J. Chem. Soc. Perkin Trans. 1 1994, 1651. (g) Sun, L. D. ; Tu, Y. Q. Tetrahedron Lett. 1998, 39, 7935. (h) Blay, G. ; Bargues, V. ; Cardona, L. ; Collado, A. M. ; García, B. ; Muñoz, M. C. ; Pedro, J. R. J. Org. Chem. 2000, 65, 2138. (i) Blay, G. ; Bargues, V. ; Cardona, L. ; García, B. ; Pedro, J. R. J. Org. Chem. 2000, 65, 6703. (j) Blay, G. ; Bargues, V. ; Cardona, L. ; García, B. ; Pedro, J. R. Tetrahedron 2001, 57, 9719. (k) Blay, G. ; Cardona, L. ; García, B. ; Lahoz, L. ; Pedro, J. R. J. Org. Chem. 2001, 66, 7700. (l) Xia, W. J. ; Li, D. R. ; Tu, Y. Q. Synth. Commun. 2001, 31, 1613. (m) Xia, W. J. ; Sun, L. D. ; Shi, L. ; Zhang, S. Y. ; Tu, Y. Q. Chin. J. Chem. 2004, 22, 377. (n) Makiyi, E. F. ; Frade, R. F. M. ; Lebl, T. ; Jaffray, E. G. ; Cobb, S. E. ; Harvey, A. L. ; Slawin, A. M. Z. ; Hay, R. T. ; Westwood, N. J. Eur. J. Org. Chem. 2009, 2009, 5711. (o) Dai, X. L. ; Tang, J. ; Zhang, L. Q. ; Tao, L. Z. ; Ouyang, Z. ; Wang, M. Chin. J. Org. Chem. 2015, 35, 2142. (戴笑丽, 汤建, 章凌琼, 陶连芝, 欧阳臻, 王民, 有机化学, 2015, 35, 2142. )
(a) Natarajan, A. ; Tsai, C. K. ; Khan, S. I. ; McCarren, P. ; Houk, K. N. ; Garcia-Garibay, M. A. J. Am. Chem. Soc. 2007, 129, 9846. (b) Commins, P. ; Natarajan, A. ; Tsai, C. K. ; Khan, S. I. ; Nath, N. K. ; Naumov, P. ; Garcia-Garibay, M. A. Cryst. Growth Des. 2015, 15, 1983. (c) Chen, X. ; Tian, G. J. ; Rinkevicius, Z. ; Vahtras, O. ; Cao, Z. X. ; Ågren, H. ; Luo, Y. Chem. Phys. 2012, 405, 40. (d) Chen, X. ; Rinkevicius, Z. ; Luo, Y. ; Ågren, H. ; Cao, Z. X. ChemPhysChem 2012, 13, 353.
(a) Herout, V. ; Sorm, F. Collect. Czech. Chem. Commun. 1953, 18, 854. (b) Herout, V. ; Sorm, F. Collect. Czech. Chem. Commun. 1954, 19, 792. (c) Novotny, L. ; Herout, V. ; Sorm, F. Collect. Czech. Chem. Commun. 1960, 25, 1492 and references therein.
Zhang, W. H.; Luo, S. J.; Fang, F.; Chen, Q. S.; Hu, H. W.; Jia, X. S.; Zhai, H. B. J. Am. Chem. Soc. 2005, 127, 18.
doi: 10.1021/ja0439219
Vokac, K.; Samek, Z.; Herout, V.; Sorm, F. Tetrahedron Lett. 1968, 9, 3855.
doi: 10.1016/S0040-4039(01)99119-1
Li, C.; Yu, X. L.; Lei, X. G. Org. Lett. 2010, 12, 4284.
doi: 10.1021/ol101705j
Wu, Z. J.; Xu, X. K.; Shen, Y. H.; Su, J.; Tian, J. M.; Liang, S.; Li, H. L.; Liu, R. H.; Zhang, W. D. Org. Lett. 2008, 10, 2397.
doi: 10.1021/ol800656q
Doyle, A. G.; Jacobsen, E. N. Chem. Rev. 2007, 107, 5713.
doi: 10.1021/cr068373r
(a) Li, C. ; Dian, L. Y. ; Zhang, W. D. ; Lei, X. G. J. Am. Chem. Soc. 2012, 134, 12414. (b) Li, C. ; Dong, T. ; Dian, L. Y. ; Zhang, W. D. ; Lei, X. G. Chem. Sci. 2013, 4, 1163. (c) Li, C. ; Lei, X. G. J. Org. Chem. 2014, 79, 3289. (d) Li, C. ; Dong, T. ; Li, Q. ; Lei, X. G. Angew. Chem. Int. Ed. 2014, 53, 12111.
Xia, D. L.; Du, Y.; Yi, Z.; Song, H.; Qin, Y. Chem. Eur. J. 2013, 19, 4423.
doi: 10.1002/chem.201204292
(a) Bohlmann, F. ; Ahmed, M. ; Jakupovic, J. ; King, R. M. ; Robinson, H. Phytochemistry 1983, 22, 191. (b) Bohlmann, F. ; Zdero, C. ; Hirschmann-Schmeda, G. ; Jakupovic, J. ; Dominguez, X. A. ; King, R. M. ; Robinson, H. Phytochemistry 1986, 25, 1175. (c) Wang, Y. ; Shen, Y. H. ; Jin, H. Z. ; Fu, J. J. ; Hu, X. J. ; Qin, J. J. ; Liu, J. H. ; Chen, M. ; Yan, S. K. ; Zhang, W. D. Org. Lett. 2008, 10, 5517.
(a) Chu, H. ; Smith, J. M. ; Felding, J. ; Baran, P. S. ACS Cent. Sci. 2017, 3, 47. For other related synthesis, see: (b) Oliver, S. F. ; Högenauer, K. ; Simic, O. ; Antonello, A. ; Smith, M. D. ; Ley, S. V. Angew. Chem. Int. Ed. 2003, 42, 5996. (c) Ball, M. ; Andrews, S. P. ; Wierschem, F. ; Cleator, E. ; Smith, M. D. ; Ley, S. V. Org. Lett. 2007, 9, 663. (d) Chen, D. Z. ; Evans, P. A. J. Am. Chem. Soc. 2017, 139, 6046.
(a) Rasmussen, U. ; Christensen, S. B. Acta Pharm. Suec. 1978, 15, 133. (b) Smitt, U. W. ; Christensen, S. B. Planta Med. 1991, 57, 196. (c) Liu, H. ; Jensen, K. G. ; Tran, L. M. ; Chen, M. ; Zhai, L. ; Olsen, C. E. ; Søhoel, H. ; Denmeade, S. R. ; Isaacs, J. T. ; Christensen, S. B. Phytochemistry 2006, 67, 2651.
Thastrup, O.; Cullen, P. J.; Drøbak, B. K.; Hanley, M. R.; Dawson, A. P. Proc. Natl. Acad. Sci. U. S. A. 1990, 87, 2466.
doi: 10.1073/pnas.87.7.2466
Hergenhahn, M.; Adolf, W.; Hecker, E. Tetrahedron Lett. 1975, 16, 1595.
Wender, P. A.; Jesudason, C. D.; Nakahira, H.; Tamura, N.; Tebbe, A. L.; Ueno, Y. J. Am. Chem. Soc. 1997, 119, 12976.
doi: 10.1021/ja972279y
Jackson, S. R.; Johnson, M. G.; Mikami, M.; Shiokawa, S.; Carreira, E. M. Angew. Chem., Int. Ed. 2001, 40, 2694.
doi: 10.1002/(ISSN)1521-3773
Flekhter, O. B.; Nigmatullina, L. R.; Baltina, L. A.; Karachurina, L. T.; Galin, F. Z.; Zarudii, F. S.; Tolstikov, G. A.; Boreko, E. I.; Pavlova, N. I.; Nikolaeva, S. N.; Savinova, O. V. Pharm. Chem. J. 2002, 36, 484.
doi: 10.1023/A:1021844705853
Al-Dabbas, M. M.; Hashinaga, F.; Abdelgaleil, S. A. M.; Suganuma, K.; Akiyama, H. H. J. Ethnopharmacol. 2005, 97, 237.
doi: 10.1016/j.jep.2004.11.007
Shi, Y. S.; Liu, Y. B.; Ma, S. G.; Li, Y.; Qu, J.; Li, L.; Yuan, S. P.; Hou, Q.; Li, Y. H.; Jiang, J. D.; Yu, S. S. J. Nat. Prod. 2015, 78, 1526.
doi: 10.1021/np500951s
Li, D. L.; Zheng, X.; Chen, Y. C.; Jiang, S.; Zhang, Y.; Zhang, W. M.; Wang, H. Q.; Du, Z. Y.; Zhang, K. Arch. Pharm. Res. 2016, 39, 51.
doi: 10.1007/s12272-015-0655-y
Komaki, H.; Tanaka, Y.; Yazawa, K.; Takagi, H.; Ando, A.; Nagata, Y.; Mikami, Y. J. Antibiot. 2000, 53, 75.
doi: 10.7164/antibiotics.53.75
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