Chinese Journal of Organic Chemistry ›› 2019, Vol. 39 ›› Issue (11): 3105-3113.DOI: 10.6023/cjoc201904071 Previous Articles Next Articles
收稿日期:
2019-04-29
发布日期:
2019-07-09
通讯作者:
杨震
E-mail:yangzhen09@usx.edu.cn
基金资助:
Zhang Liu, Zhang Mengfan, Qi Chenze, Yang Zhen*()
Received:
2019-04-29
Published:
2019-07-09
Contact:
Yang Zhen
E-mail:yangzhen09@usx.edu.cn
Supported by:
Share
Zhang Liu, Zhang Mengfan, Qi Chenze, Yang Zhen. Synthetic Studies toward Natural Occurred Cyanolide A and Cocosolide[J]. Chinese Journal of Organic Chemistry, 2019, 39(11): 3105-3113.
[1] |
Newman D. J. Cragg G. M. J. Nat. Prod. 2016 79 629.
doi: 10.1021/acs.jnatprod.5b01055 |
[2] |
Giordanetto F. Kihlberg J. J. Med. Chem. 2014 57 278.
doi: 10.1021/jm400887j |
[3] | McGuire J. M. Bunch R. L. Anderson R. C. Boaz H. E. Flynn E. H. Powell H. M. Smith J. W. Antibiot. Chemother. 1952 2 281. |
[4] |
Altmann K.-H. Gaugaz F. Z. Schiess R. Mol. Diversity 2011 15 383.
doi: 10.1007/s11030-010-9291-0 |
[5] |
Seiple I. B. Zhang Z. Y. Jakubec P. Langlois-Mercier A. Wright P. M. Hog D. T. Yabu K. Z. Allu S. R. Fukuzaki T. Carlsen P. N. Kitamura Y. Zhou X. Condakes M. L. Szczypiński F. T. Green W. D. Myers A. G. Nature 2016 533 338.
doi: 10.1038/nature17967 |
[6] |
Pereira A. R. McCue C. F. Gerwick W. H. J. Nat. Prod. 2010 73 217.
doi: 10.1021/np9008128 |
[7] |
Gunaseker S. P. Li Y. Ratnayake R. Luo D. M. Lo J. Reibenspies J. H. Xu Z. S. Clare-Salzler M. J. Ye T. Paul V. J. Luesch H. Chem.-Eur. J. 2016 22 8158.
doi: 10.1002/chem.201600674 |
[8] |
Rao R. M. Faulkner D. J. J. Nat. Prod. 2002 65 386.
doi: 10.1021/np010495l |
[9] |
Steinmann P. Keiser J. Bos R. Tanner M. Utzinger J. Lancet. Infect. Dis. 2006 6 411.
doi: 10.1016/S1473-3099(06)70521-7 |
[10] |
Chitsulo L. Engels D. Montresor A. Savioli L. Acta Trop. 2000 77 41.
doi: 10.1016/S0001-706X(00)00122-4 |
[11] | World Health Organization Report of the Scientific Working Group Meeting on Schistosomiasis, Geneva, Switzerland, November 14~16, 2005. |
[12] |
(a) Hong, J.; Kim, H. Org. Lett. 2010, 12, 2880.
doi: 10.1021/ol101022z |
(b) Hajare, A. K.; Ravikumar, V.; Khaleel, S.; Bhuniya, D.; Reddy, D. S. J. Org. Chem. 2011, 76, 963.
doi: 10.1021/ol101022z |
|
(c) Yang, Z.; Xie, X.; Jing, P.; Zhao, G.; Zheng, J.; Zhao, C.; She, X. Org. Biomol. Chem. 2011, 9, 984.
doi: 10.1021/ol101022z |
|
(d) Pabbaraja, S.; Satyanarayana, K.; Ganganna, B.; Yadav, J. S. J. Org. Chem. 2011, 76, 1922.
doi: 10.1021/ol101022z |
|
(e) Gesinski, M. R.; Rychnovsky, S. D. J. Am. Chem. Soc. 2011, 133, 9727.
doi: 10.1021/ol101022z |
|
(f) Sharpe, R. J.; Jennings, M. P. J. Org. Chem. 2011, 76, 8027.
doi: 10.1021/ol101022z |
|
(g) Tay, G. C.; Gesinski, M. R.; Rychnovsky, S. D. Org. Lett. 2013, 15, 4536.
doi: 10.1021/ol101022z |
|
(h) Waldeck, A. R.; Krische, M. J. Angew. Chem., Int. Ed. 2013, 52, 4470.
doi: 10.1021/ol101022z |
|
(i) Bates, R. W.; Lek, T. G. Synthesis 2014, 46, 1731.
doi: 10.1021/ol101022z |
|
(j) Che, W.; Li, Y. Z.; Liu, J. C.; Zhu, S. F.; Xie, J. H.; Zhou, Q. L. Org. Lett. 2019, 21, 2369.
doi: 10.1021/ol101022z |
|
(j) Lee, K.; Lanier, M. L.; Kwak, J. H.; Kim, H.; Hong, J. Y. Nat. Prod. Rep. 2016, 33, 1393.
doi: 10.1021/ol101022z |
|
[13] | (a) Ye, T.; Xu, Z.; Li, Y.; Luesch, H.; Paul, V. J.; Gunasekera, S. P. CN 105884843, 2016. |
(b) Luesch, H.; Paul, V. J.; Gunasekera, S. WO 2017152099, 2017. | |
[14] | Armesto D. Horspool W. M. Gallego M. G. Agarrabeitia A. R. J. Chem. Soc., Perkin Trans. 1 1992 163. |
[15] |
Mohapatra D. K. Das P. P. Reddy D. S. Yadav J. S. Tetrahedron Lett. 2009 50 5941.
doi: 10.1016/j.tetlet.2009.08.028 |
[16] | Barry C. S. Bushby N. Charmant J. P. H. Elsworth J. D. Harding J. R. Willis C. L. Chem. Commun. 2005 5097. |
[17] |
(a) Nugent, W. A. Chem. Commun. 1999, 1369.
doi: 10.1021/ja027271p |
(b) Chen, Y. K.; Lurain, A. E.; Walsh, P. J. J. Am. Chem. Soc. 2002, 124, 12225.
doi: 10.1021/ja027271p |
|
[18] |
Shiina I. Kubota M. Oshiumi H. Hashizume M. J. Org. Chem. 2004 69 1822.
doi: 10.1021/jo030367x |
[19] |
Ball M. Baron A. Bradshaw B. Omori H. MacCormick S. Thomas E. J. Tetrahedron Lett. 2004 45 8737.
doi: 10.1016/j.tetlet.2004.09.124 |
[20] |
Liu J. Yang J. H. Ko C. Hsung R. P. Tetrahedron Lett. 2006 47 6121.
doi: 10.1016/j.tetlet.2006.06.067 |
[21] |
Inanaga J. Hirata K. Saeki H. Katsuki T. Yamaguchi M. Bull. Chem. Soc. Jpn. 1979 52 1989.
doi: 10.1246/bcsj.52.1989 |
[22] |
Crimmins M. T. Emmitte K. A. Org. Lett. 1999 1 2029.
doi: 10.1021/ol991201e |
[23] |
Corey E. J. Bakshi R. K. Shibata S. J. Am. Chem. Soc. 1987 109 5551.
doi: 10.1021/ja00252a056 |
[24] |
(a) Bower, J. F.; Kim, I. S.; Patman, R. L.; Krische, M. J. Angew. Chem., Int. Ed. 2008, 48, 34.
doi: 10.1002/anie.200802938 |
(b) Patman, R. L.; Bower, J. F.; Kim, I. S.; Krische, M. J. Aldrichim. Acta 2008, 41, 95.
doi: 10.1002/anie.200802938 |
|
(c) Han, S. B.; Kim, I. S.; Krische, M. J. Chem. Commun. 2009, 7278.
doi: 10.1002/anie.200802938 |
|
[25] |
Fuwa H. Noto K. Sasaki M. Org. Lett. 2011 13 1820.
doi: 10.1021/ol200333p |
[26] |
Fuwa H. Heterocycles 2012 85 1255.
doi: 10.3987/REV-12-730 |
[27] |
Pirrung M. C. Kenney P. M. J. Org. Chem. 1987 52 2335.
doi: 10.1021/jo00387a053 |
[28] |
(a) Che, W.; Wen, D. C.; Zhu, S. F.; Zhou, Q. L. Org. Lett. 2018, 20, 3305.
doi: 10.1021/acs.orglett.8b01193 |
(b) Bao, D. H.; Wu, H. L.; Liu, C.-L.; Xie, J. H.; Zhou, Q. L. Angew. Chem., Int. Ed. 2015, 54, 8791.
doi: 10.1021/acs.orglett.8b01193 |
|
[29] |
Sun J. Dong Y. Cao L. Wang X. Wang S. Hu Y. J. Org. Chem. 2004 69 8932.
doi: 10.1021/jo0486239 |
[30] |
Schaus S. E. Brandes B. D. Larrow J. F. Tokunaga M. Hansen K. B. Gould A. E. Furrow M. E. Jacobsen E. N. J. Am. Chem. Soc. 2002 124 1307.
doi: 10.1021/ja016737l |
[31] |
Nicolaou K. C. Li A. Edmonds D. J. Tria S. Ellery S. P. J. Am. Chem. Soc. 2009 131 16905.
doi: 10.1021/ja9068003 |
[32] |
Zhang Y. Sammakia T. J. Org. Chem. 2006 71 6262.
doi: 10.1021/jo0605694 |
[33] |
VanRheenen V. Kelly R. C. Cha D. Y. Tetrahedron Lett. 1976 17 1973.
doi: 10.1016/S0040-4039(00)78093-2 |
[34] |
(a) Evans, D. A.; Gauchet-Prunet, J. A. J. Org. Chem., 1993, 58, 2446.
doi: 10.1021/jo00061a018 |
(b) Rotulo-Sims, D.; Prunet, J. Org. Lett. 2007, 9, 4147
doi: 10.1021/jo00061a018 |
|
[35] |
Evans D. A. Dart M. J. Duffy J. L. Yang M. G. J. Am. Chem. Soc. 1996 118 4322.
doi: 10.1021/ja953901u |
[36] |
Narasaka K. Pai F. C. Tetrahedron 1984 40 2233.
doi: 10.1016/0040-4020(84)80006-X |
[37] |
Evans D. A. Hoveyda A. H. J. Am. Chem. Soc. 1990 112 6447.
doi: 10.1021/ja00173a071 |
[38] |
Petrier C. Luche J. L. J. Org. Chem. 1985 50 910.
doi: 10.1021/jo00206a047 |
[39] |
White J. D. Hong J. Robarge L. A. Tetrahedron Lett. 1999 40 1463.
doi: 10.1016/S0040-4039(98)02693-8 |
[40] |
Gao D. O'Doherty G. A. J. Org. Chem. 2005 70 9932.
doi: 10.1021/jo051681p |
[41] |
Reiff E. A. Nair S. K. Henri J. T. Greiner J. F. Reddy B. S. Chakrasali R. David S. A. Chiu T.-L. Amin E. A. Himes R. H. Vander Velde D. G. Georg G. I. J. Org. Chem. 2010 75 86.
doi: 10.1021/jo901752v |
[42] |
(a) Armstrong, A.; Scutt, J. N. Org. Lett. 2003, 5, 2331.
doi: 10.1021/ol0346887 |
(b) Armstrong, A.; Scutt, J. N. Chem. Commun. 2004, 510.
doi: 10.1021/ol0346887 |
|
(c) Delhaye, L.; Merschaert, A.; Delbeke, P.; Briúne, W. Org. Process Res. Dev. 2007, 11, 689.
doi: 10.1021/ol0346887 |
|
(d) Bray, C. D.; Minicone, F. Chem. Commun. 2010, 46, 5867.
doi: 10.1021/ol0346887 |
|
(e) Kumar, P.; Dubey, A.; Harbindu, A. Org. Biomol. Chem. 2012, 10, 6987.
doi: 10.1021/ol0346887 |
|
[43] |
(a) Ren, R. G.; Mao, Z. Y.; Wei, B. G.; Lin, G. G. Chin. J. Org. Chem. 2015, 35, 2313 (in Chinese).
doi: 10.6023/cjoc201507033 |
(任荣国, 毛卓亚, 魏邦国, 林国强, 有机化学, 2015, 35, 2313.)
doi: 10.6023/cjoc201507033 |
|
(b) Yu, J. F.; Feng, R. K.; Yang, Z. Chin. J. Org. Chem. 2017, 37, 2526 (in Chinese).
doi: 10.6023/cjoc201507033 |
|
(于江帆, 冯若昆, 杨震, 有机化学, 2017, 37, 2526.
doi: 10.6023/cjoc201507033 |
|
[44] |
Shi D. X. Feng X. Zhuang X. L. Chai H. X. Liu T. Zhang Q. Li J. R. Chin. J. Org. Chem. 2014 34 2543.
doi: 10.6023/cjoc201405007 |
史 大昕 冯 雪 庄 晓磊 柴 洪新 刘 霆 张 奇 李 加荣 有机化学 2014 34 2543.
doi: 10.6023/cjoc201405007 |
[1] | Han Jilai, Tang Meilin, Sun Xun. Study on the Total Synthesis of Resveratrol Dimers Quadrangularin A and Pallidol [J]. Chinese Journal of Organic Chemistry, 2020, 40(6): 1571-1577. |
[2] | Dong Wei, Wang Xin, Ge Zemei, He Fang, Li Runtao. Efficient Synthesis of Wogonin [J]. Chinese Journal of Organic Chemistry, 2020, 40(6): 1725-1730. |
[3] | Xie Tao, He Haibing, Gao Shuanhu. Synthetic Progress of Polycyclic Xanthone [J]. Chinese Journal of Organic Chemistry, 2020, 40(3): 551-562. |
[4] | Sun Zezhong, Xu Miao, Wang Yunxia, Hu Xiangdong. Synthetic Progress of Alkaloids against Mycobacterium Tuberculosis: Pseudopteroxazole and Ileabethoxazole [J]. Chinese Journal of Organic Chemistry, 2020, 40(12): 4203-4215. |
[5] | Li Ying, Ma Zhiqiang, Xu Xuetao. Application of tert-Butanesulfinamide in Total Synthesis of Natural Products [J]. Chinese Journal of Organic Chemistry, 2020, 40(12): 3991-4014. |
[6] | Wang Lu-Ning, Yu Zhi-Xiang. Transition-Metal-Catalyzed Cycloadditions for the Synthesis of Eight-Membered Carbocycles: an Update from 2010 to 2020 [J]. Chinese Journal of Organic Chemistry, 2020, 40(11): 3536-3558. |
[7] | Li Jian, He Long, Zhou Zhiqiang, Zhen Yanxia, Xie Weiqing. Advances in the Synthesis of Anislactone-Type Sesquiterpenes [J]. Chinese Journal of Organic Chemistry, 2020, 40(10): 3166-3176. |
[8] | 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. |
[9] | Chen Si, Zhao Yanchuan. C(sp3)—C(sp3) Bond Formation via Transition-Metal Mediated and Catalyzed Reductive Homocouplings [J]. Chinese Journal of Organic Chemistry, 2020, 40(10): 3078-3093. |
[10] | Tang Jie, Dong Xiangyou, Ouyang Wenliang, Zhu Yunlong, Ding Haixin, Xiao Qiang. Studies on the Total Synthesis of iso-L-Guanosine [J]. Chin. J. Org. Chem., 2019, 39(9): 2609-2615. |
[11] | Zhang Yan, Guo Liandong, Xu Jing. Efficient Synthesis of the AC Ring System of Daphnilactone B [J]. Chin. J. Org. Chem., 2019, 39(4): 1079-1084. |
[12] | Zhang Kun, Xu Hongjin, Liu Zibo, Song Chuanjun. Total Synthesis of Carbazole Alkaloid Murrayaquinone A [J]. Chin. J. Org. Chem., 2019, 39(4): 1142-1146. |
[13] | Guo, Dongdong, Zhang, Wuxia, Gao, Weimei, Guo, Xiaodi, Wang, Yongqiang. Total Synthesis of Pulchrol and Pulchral [J]. Chinese Journal of Organic Chemistry, 2019, 39(10): 2936-2940. |
[14] | Shen Xianfu, Peng Tianfeng, Zhou Yongyun, Xi Yongkai, Zhao Jingfeng, Yang Xiaodong, Zhang Hongbin. Progress in Total Syntheses of Dimeric Cyclotryptamine Alkaloids [J]. Chinese Journal of Organic Chemistry, 2019, 39(10): 2685-2704. |
[15] | Sun Mao, Qiu Fayang, Li Wei-Dong. Recent Progresses in the Synthesis of Solanoeclepin A [J]. Chinese Journal of Organic Chemistry, 2019, 39(10): 2759-2770. |
Viewed | ||||||
Full text |
|
|||||
Abstract |
|
|||||