Synthetic Progress of Natural Products Gracilioethers and Hippolachnin A
- Corresponding author: Ma Zhiqiang, cezqma@scut.edu.cn
Citation:
Wu Jinghua, Wang Cheng, Chen Pengquan, Ma Zhiqiang. Synthetic Progress of Natural Products Gracilioethers and Hippolachnin A[J]. Chinese Journal of Organic Chemistry,
;2020, 40(10): 3289-3299.
doi:
10.6023/cjoc202003014
Cragg, G. M.; Newman, D. J. Biochim. Biophys. Acta, Gen. Subj. 2013, 1830, 3670.
doi: 10.1016/j.bbagen.2013.02.008
Ueoka, R.; Nakao, Y.; Kawatsu, S.; Yaegashi, J.; Matsumoto, Y.; Matsunaga, S.; Furihata, K.; Soest, R. W. M. V.; Fusetani, N. J. Org. Chem. 2009, 74, 4203.
doi: 10.1021/jo900380f
Festa, C.; Lauro, G.; De Marino, S.; D'Auria, M. V.; Monti, M. C.; Casapullo, A.; D'Amore, C.; Renga, B.; Mencarelli, A.; Petek, S.; Bifulco, G.; Fiorucci, S.; Zampella, A. J. Med. Chem. 2012, 55, 8303.
doi: 10.1021/jm300911g
(a) Festa, S.; De Marino, S.; D'Auria, M. V.; Deharo, E.; Gonzalez, G.; Deyssard, C.; Petek, S.; Bifulco, G.; Zampella, A. Tetrahedron 2012, 68, 10157.
(b) Festa, C.; D'Amore, C.; Renga, B.; Lauro, G.; De Marino, S.; D'Auria, M. V.; Bifulco, G.; Zampella, A.; Fiorucci, S. Mar. Drugs 2013, 11, 2314.
Piao, S.; Song, Y.; Jiao, W.; Yang, F.; Liu, X.; Chen, W.; Han, B.; Lin, H. Org. Lett. 2013, 15, 3526.
doi: 10.1021/ol400933x
(a) Lee-Ruff, E.; Mladenova, G. Chem. Rev. 2003, 103, 1449.
(b) Poplata, S.; Tröster, A.; Zou, Y.-Q.; Bach, T. Chem. Rev. 2016, 116, 9748.
(c) Salomon, R. G. Tetrahedron 1983, 39, 485.
Rasik, C. M.; Brown, M. K. Angew. Chem., Int. Ed. 2014, 53, 14522.
doi: 10.1002/anie.201408055
Ruider, S. A.; Sandmeier, T.; Carreira, E. M. Angew. Chem., Int. Ed. 2015, 54, 2378.
doi: 10.1002/anie.201410419
Ruider, S. A.; Carreira, E. M. Org. Lett. 2016, 18, 220.
doi: 10.1021/acs.orglett.5b03356
McCallum, M. E.; Rasik, C. M.; Wood, J. L.; Brown, M. K. J. Am. Chem. Soc. 2016, 138, 2437.
doi: 10.1021/jacs.5b13586
Xu, Z. J.; Wu, Y. Chem.-Eur. J. 2017, 23, 2026.
doi: 10.1002/chem.201605776
Li, Q.; Zhao, K.; Peuronen, A.; Rissanen, K.; Enders, D.; Tang, Y. J. Am. Chem. Soc. 2018, 140, 1937.
doi: 10.1021/jacs.7b12903
Shen, X.; Peng, X.; Wong, H. N. C. Org. Lett. 2016, 18, 1032.
doi: 10.1021/acs.orglett.6b00161
Winter, N.; Trauner, D. J. Am. Chem. Soc. 2017, 139, 11706.
doi: 10.1021/jacs.7b06815
Datta, R.; Ghosh, S. J. Org. Chem. 2017, 82, 7675.
doi: 10.1021/acs.joc.7b01179
(a) Rasik, C. M.; Brown M. K. J. Am. Chem. Soc. 2013, 135, 1673.
(b) Rasik, C. M.; Brown, M. K. Synlett 2014, 760.
(c) Wang, Y.; Wei, D.; Li, Z.; Zhu, Y.; Tang, M. J. Phys. Chem. A 2014, 118, 4288.
(d) Rasik, C. M.; Hong, Y. J.; Tantillo, D. J.; Brown, M. K. Org. Lett. 2014, 16, 5168.
(e) Huston, R.; Rey, M.; Dreiding, A. S. Helv. Chim. Acta 1982, 65, 1563.
(f) Nelson, S. G.; Dura, R. D.; Peelen, T. J. Org. React. 2012, 82, 471.
(g) Loebach, J. L.; Bennett, D. M.; Danheiser, R. L. J. Org. Chem. 1998, 63, 8380.
(a) Godula, K. Science 2006, 312, 67.
(b) Gutekunst, W. R.; Baran, P. S. Chem. Soc. Rev. 2011, 40, 1976.
(c) Newhouse, T.; Baran, P. S. Angew. Chem., Int. Ed. 2011, 50, 3362.
(a) Chen, M. S.; White, M. C. Science 2007, 318, 783.
(b) Bigi, M. A.; Reed, S. A.; White, M. C. J. Am. Chem. Soc. 2012, 134, 9721.
(c) Shi, G.; Zhang, Y. Adv. Synth. Catal. 2014, 356, 1419.
(a) Song, L.; Yao, H.; Zhu, L.; Tong, R. Org. Lett. 2013, 15, 6.
(b) Noyori, R.; Tomino, I.; Yamada, M.; Nishizawa, M. J. Am. Chem. Soc. 1984, 106, 6717.
(a) Dias, E. L.; Brookhart, M.; White, P. S. Chem. Commun. 2001, 423.
(b) Gao, H.; Zhang, J. Chem.-Eur. J. 2012, 18, 2777.
(a) Smith, C. D. J. Am. Chem. Soc. 1966, 88, 4273.
(b) Tabushi, I.; Yamamura, K.; Yoshida, Z. J. Am. Chem. Soc. 1972, 94, 787.
(c) Petrov, V. A.; Vasil'ev, N. V. Curr. Org. Synth. 2006, 3, 215.
(a) Osberger, T. J.; White, M. C. J. Am. Chem. Soc. 2014, 136, 11176.
(b) Ammann, S. E.; Rice, G. T.; White, M. C. J. Am. Chem. Soc. 2014, 136, 10834.
(c) Malik, M.; Witkowski, G.; Jaroz, S. Org. Lett. 2014, 16, 3816.
(d) White, M. C. J. Am. Chem. Soc. 2013, 135, 14052.
Morrill, L. A.; Susick, R. B.; Chari, J. V.; Garg, N. K. J. Am. Chem. Soc. 2019, 141, 12423.
doi: 10.1021/jacs.9b05588
Kiyama, M.; Isoda, Y.; Nishimoto, M.; Kobayashi, A.; Togawa, D.; Hirao, N.; Kuboki, A.; Ohira, S.; Tetrahedron Lett. 2005, 46, 7483.
doi: 10.1016/j.tetlet.2005.09.011
Fu, C.; Ma, S. Eur. J. Org. Chem. 2005, 2005, 3942.
doi: 10.1002/ejoc.200500296
(a) Blay, G.; Garcia, B.; Molina, E.; Pedro, J. R. Org. Lett. 2005, 7, 3291.
(b) Paquette, L. A.; Green, K. E.; Gleiter, R.; Schäfer, W.; Gallucci, J. C. J. Am. Chem. Soc. 1984, 106, 8232.
Dauben, W. G.; Koch, K.; Smith, S. L.; Chapman, O. L. J. Am. Chem. Soc. 1963, 85, 2616.
doi: 10.1021/ja00900a021
Reetz, M. T.; Chatziiosifidis, I.; Schwellnus, K. Angew. Chem. 1981, 93, 716.
doi: 10.1002/ange.19810930837
(a) RajanBabu, T. V.; Nugent, W. A. J. Am. Chem. Soc. 1994, 116, 986.
(b) RajanBabu, T. V.; Nugent, W. A.; Beattie, M. S. J. Am. Chem. Soc. 1990, 112, 6408.
(c) RajanBabu, T. V.; Nugent, W. A. J. Am. Chem. Soc. 1989, 111, 4525.
(d) Nugent, W. A.; RajanBabu, T. V. J. Am. Chem. Soc. 1988, 110, 8561.
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