Asymmetric Total Synthesis and Absolute Configuration Reassignment of Indole Alkaloid (+)-Alsmaphorazine D
- Corresponding author: Ding Hanfeng, hfding@zju.edu.cn
Citation: Yu Kuan, Gao Beiling, Ding Hanfeng. Asymmetric Total Synthesis and Absolute Configuration Reassignment of Indole Alkaloid (+)-Alsmaphorazine D[J]. Acta Chimica Sinica, ;2016, 74(5): 410-414. doi: 10.6023/A16020102
Marini-Bettolo, G. B.; Nicoletti, M.; Messana, I.; Patamia, M.; Galeffi, C.; Oguakwa, J. U.; Portalone, G.; Vaciago, A. Tetrahedron 1983, 39, 323.(b) Ghedira, K.; Zeches-Hanrot, M.; Richard, B.; Massiot, G.; Le Men-Olivier, L.; Sevenet, T.; Goh, S. H. Phytochemistry 1988, 27, 3955.(c) Cai, X. H.; Du, Z. Z.; Luo, X. D. Org. Lett. 2007, 9, 1817.
Kamarajan, P.; Sekar, N.; Mathuram, V.; Govindasamy, S. Biochem. Int. 1991, 25, 491.(b) Saraswathi, V.; Subramanian, S.; Ramamoorthy, N.; Mathuram, V.; Govindasamy, S. Med. Sci. Res. 1997, 25, 167.(c) Husain, K.; Jantan, I.; Kamaruddin, N.; Said, I. M.; Aimi, N.; Takayama, H. Phytochemistry 2001, 57, 603.(d) Khan, M. R.; Omoloso, A. D.; Kihara, M. Fitoterapia 2003, 74, 736.(e) Gupta, R. S.; Bhatnager, A. K.; Joshi, Y. C.; Sharma, M. C.; Khushalani, V.; Kachhawa, J. B. S. Pharmacology 2005, 75, 57.(f) Jagetia, G. C.; Baliga, M. S. Phytother. Res. 2006, 20, 103.
For reviews, see: (a) Liu, J.-L. Chin. J. Org. Chem. 2003, 23, 784. (刘建利, 有机化学, 2003, 23, 784).(b) Zhou, H.; Liu, J.; Wang, C. Chin. J. Org. Chem. 2010, 30, 1305. (周华凤, 刘建利, 王翠玲, 有机化学, 2010, 30, 1305).(c) Wang, X.; Liu, J.; Huang, X.; Wang, C. Chin. J. Org. Chem. 2012, 32, 420. (王学军, 刘建利, 黄新炜, 王翠玲, 有机化学, 2012, 32, 420).(d) Li, S.; Han, J.; Li, A. Acta Chim. Sinica 2013, 71, 295. (李森, 韩静, 李昂, 化学学报, 2013, 71, 295).
Koyama, K.; Hirasawa, Y.; Nugroho, A. E.; Kaneda, T.; Hoe, T. C.; Chan, K.-L.; Morita, H. Tetrahedron 2012, 68, 1502. For the isolation of alsmaphorazines A and B, see:(b) Koyama, K.; Hirasawa, Y.; Nugroho, A. E.; Hosoya, T.; Hoe, T. C.; Chan, K.-L.; Morita, H. Org. Lett. 2010, 12, 4188.
Zhu, C.; Liu, Z.; Chen, G.; Zhang, K.; Ding, H. Angew. Chem., Int. Ed. 2015, 54, 879. For the total synthesis of (±)-alsmaphorazine B, see:(b) Hong, A. Y.; Vanderwal, C. D. J. Am. Chem. Soc. 2015, 137, 7306.
Liu, X.; Cook, J. M. Org. Lett. 2001, 3, 4023.(b) Liao, X.; Zhou, H.; Wearing, X. Z.; Ma, J.; Cook, J. M. Org. Lett. 2005, 7, 3501.(c) Yin, W.; Kabir, M. S.; Wang, Z.; Rallapalli, S. K.; Ma, J.; Cook, J. M. J. Org. Chem. 2010, 75, 3339.(d) Edwankar, R. V.; Edwankar, C. R.; Deschamps, J.; Cook, J. M. Org. Lett. 2011, 13, 5216.
Kamenecka, T. M.; Danishefsky, S. J. Chem. Eur. J. 2001, 7, 41.(b) Trzupek, J. D.; Lee, D.; Crowley, B. M.; Marathias, V. M.; Danishefsky, S. J. J. Am. Chem. Soc. 2010, 132, 8506.
Peng, Q.-L.; Luo, S.-P.; Xia, X.-E.; Liu, L.-X.; Huang, P.-Q. Chem. Commun. 2014, 50, 1986.(b) Mao, Z.-Y.; Geng, H.; Zhang, T.-T.; Ruan, Y.-P.; Ye, J.-L.; Huang, P.-Q. Org. Chem. Front. 2016, 3, 24.
For selected examples, see: (a) Kamenecka, T. M.; Danishefsky, S. J. Angew. Chem., Int. Ed. 1998, 37, 2995.(b) Baran, P. S.; Guerrero, C. A.; Corey, E. J. J. Am. Chem. Soc. 2003, 125, 5628.(c) Umehara, A.; Ueda, H.; Tokuyama, H. Org. Lett. 2014, 16, 2526.
Snider, B. B. Chem. Rev. 1996, 96, 339.(b) Tsai, A.-I.; Lin, C.-H.; Chuang, C.-P. Heterocycles 2005, 65, 2381.
For the preparation, see: (a) Ma, C.; Liu, X.; Li, X.; Flippen-Anderson, J.; Yu, S.; Cook, J. M. J. Org. Chem. 2001, 66, 4525.(b) Zhou, H.; Liao, X.; Yin, W.; Ma, J.; Cook, J. M. J. Org. Chem. 2006, 71, 251.
For reviews, see: Repka, L. M.; Reisman, S. E. J. Org. Chem. 2013, 78, 12314. For selected examples, see:(b) Savige, W. E. Aust. J. Chem. 1975, 28, 2275.(c) Nakagawa, M.; Hino, T. Heterocycles 1977, 6, 1675.(d) Nakagawa, M.; Kato, S.; Kataoka, S.; Hino, T. J. Am. Chem. Soc. 1979, 101, 3136.(e) Movassaghi, M.; Schmidt, M. A. Angew. Chem., Int. Ed. 2007, 46, 3725.(f) Furst, L.; Narayanam, J. M. R.; Stephenson, C. R. J. Angew. Chem., Int. Ed. 2011, 50, 9655.(g) Kim, J.; Movassaghi, M. J. Am. Chem. Soc. 2011, 133, 14940.(h) Sun, Y.; Li, R.; Zhang, W.; Li, A. Angew. Chem., Int. Ed. 2013, 52, 9201.
CCDC 1445009 (6a') contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam. ac.uk/data_request/cif.
For selected examples, see: (a) Schkeryantz, J. M.; Woo, J. C. G.; Danishefsky, S. J. J. Am. Chem. Soc. 1995, 117, 7025.(b) Schkeryantz, J. M.; Woo, J. C. G.; Siliphaivanh, P.; Depew, K. M.; Danishefsky, S. J. J. Am. Chem. Soc. 1999, 121, 11964.(c) Zhao, L.; May, J. P.; Huang, J.; Perrin, D. M. Org. Lett. 2012, 14, 90.
Boto, A.; HernÁndez, R.; SuÁrez, E. Tetrahedron Lett. 1999, 40, 5945.(b) Boto, A.; HernÁndez, R.; SuÁrez, E. Tetrahedron Lett. 2000, 41, 2495.(c) Boto, A.; HernÁndez, R.; SuÁrez, E. J. Org. Chem. 2000, 65, 4930.
See SI for the detailed characterization of compound 16.
Evans, D. A.; Fu, G. C.; Hoveyda, A. H. J. Am. Chem. Soc. 1988, 110, 6917.(b) Burgess, K.; van der Donk, W. A.; Westcott, S. A.; Marder, T. B.; Baker, R. T.; Calabrese, J. C. J. Am. Chem. Soc. 1992, 114, 9350.
Zhiwen HU , Weixia DONG , Qifu BAO , Ping LI . Low-temperature synthesis of tetragonal BaTiO3 for piezocatalysis. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 857-866. doi: 10.11862/CJIC.20230462
Chuanming GUO , Kaiyang ZHANG , Yun WU , Rui YAO , Qiang ZHAO , Jinping LI , Guang LIU . Performance of MnO2-0.39IrOx composite oxides for water oxidation reaction in acidic media. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1135-1142. doi: 10.11862/CJIC.20230459
Yuhao SUN , Qingzhe DONG , Lei ZHAO , Xiaodan JIANG , Hailing GUO , Xianglong MENG , Yongmei GUO . Synthesis and antibacterial properties of silver-loaded sod-based zeolite. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 761-770. doi: 10.11862/CJIC.20230169
Xin MA , Ya SUN , Na SUN , Qian KANG , Jiajia ZHANG , Ruitao ZHU , Xiaoli GAO . A Tb2 complex based on polydentate Schiff base: Crystal structure, fluorescence properties, and biological activity. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1347-1356. doi: 10.11862/CJIC.20230357
Jinlong YAN , Weina WU , Yuan WANG . A simple Schiff base probe for the fluorescent turn-on detection of hypochlorite and its biological imaging application. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1653-1660. doi: 10.11862/CJIC.20240154
Yonghui ZHOU , Rujun HUANG , Dongchao YAO , Aiwei ZHANG , Yuhang SUN , Zhujun CHEN , Baisong ZHU , Youxuan ZHENG . Synthesis and photoelectric properties of fluorescence materials with electron donor-acceptor structures based on quinoxaline and pyridinopyrazine, carbazole, and diphenylamine derivatives. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 701-712. doi: 10.11862/CJIC.20230373
Endong YANG , Haoze TIAN , Ke ZHANG , Yongbing LOU . Efficient oxygen evolution reaction of CuCo2O4/NiFe-layered bimetallic hydroxide core-shell nanoflower sphere arrays. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 930-940. doi: 10.11862/CJIC.20230369
Jiaqi AN , Yunle LIU , Jianxuan SHANG , Yan GUO , Ce LIU , Fanlong ZENG , Anyang LI , Wenyuan WANG . Reactivity of extremely bulky silylaminogermylene chloride and bonding analysis of a cubic tetragermylene. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1511-1518. doi: 10.11862/CJIC.20240072
Youlin SI , Shuquan SUN , Junsong YANG , Zijun BIE , Yan CHEN , Li LUO . Synthesis and adsorption properties of Zn(Ⅱ) metal-organic framework based on 3, 3', 5, 5'-tetraimidazolyl biphenyl ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1755-1762. doi: 10.11862/CJIC.20240061
Zhihuan XU , Qing KANG , Yuzhen LONG , Qian YUAN , Cidong LIU , Xin LI , Genghuai TANG , Yuqing LIAO . Effect of graphene oxide concentration on the electrochemical properties of reduced graphene oxide/ZnS. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1329-1336. doi: 10.11862/CJIC.20230447
Min WANG , Dehua XIN , Yaning SHI , Wenyao ZHU , Yuanqun ZHANG , Wei ZHANG . Construction and full-spectrum catalytic performance of multilevel Ag/Bi/nitrogen vacancy g-C3N4/Ti3C2Tx Schottky junction. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1123-1134. doi: 10.11862/CJIC.20230477
Guimin ZHANG , Wenjuan MA , Wenqiang DING , Zhengyi FU . Synthesis and catalytic properties of hollow AgPd bimetallic nanospheres. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 963-971. doi: 10.11862/CJIC.20230293
Qilu DU , Li ZHAO , Peng NIE , Bo XU . Synthesis and characterization of osmium-germyl complexes stabilized by triphenyl ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1088-1094. doi: 10.11862/CJIC.20240006
Kai CHEN , Fengshun WU , Shun XIAO , Jinbao ZHANG , Lihua ZHU . PtRu/nitrogen-doped carbon for electrocatalytic methanol oxidation and hydrogen evolution by water electrolysis. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1357-1367. doi: 10.11862/CJIC.20230350
Zhuo WANG , Junshan ZHANG , Shaoyan YANG , Lingyan ZHOU , Yedi LI , Yuanpei LAN . Preparation and photocatalytic performance of CeO2-reduced graphene oxide by thermal decomposition. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1708-1718. doi: 10.11862/CJIC.20240067
Jingjing QING , Fan HE , Zhihui LIU , Shuaipeng HOU , Ya LIU , Yifan JIANG , Mengting TAN , Lifang HE , Fuxing ZHANG , Xiaoming ZHU . Synthesis, structure, and anticancer activity of two complexes of dimethylglyoxime organotin. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1301-1308. doi: 10.11862/CJIC.20240003
Haitang WANG , Yanni LING , Xiaqing MA , Yuxin CHEN , Rui ZHANG , Keyi WANG , Ying ZHANG , Wenmin WANG . Construction, crystal structures, and biological activities of two LnⅢ3 complexes. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1474-1482. doi: 10.11862/CJIC.20240188
Jingke LIU , Jia CHEN , Yingchao HAN . Nano hydroxyapatite stable suspension system: Preparation and cobalt adsorption performance. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1763-1774. doi: 10.11862/CJIC.20240060
Limei CHEN , Mengfei ZHAO , Lin CHEN , Ding LI , Wei LI , Weiye HAN , Hongbin WANG . Preparation and performance of paraffin/alkali modified diatomite/expanded graphite composite phase change thermal storage material. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 533-543. doi: 10.11862/CJIC.20230312
Zhanggui DUAN , Yi PEI , Shanshan ZHENG , Zhaoyang WANG , Yongguang WANG , Junjie WANG , Yang HU , Chunxin LÜ , Wei ZHONG . Preparation of UiO-66-NH2 supported copper catalyst and its catalytic activity on alcohol oxidation. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 496-506. doi: 10.11862/CJIC.20230317