Enantioselective total synthesis of (+)-vincamine
-
* Corresponding authors.
E-mail addresses: songhao@scu.edu.cn (H. Song), yongqin@scu.edu.cn (Y. Qin).
Citation:
Fanglin Xue, Hengmao Liu, Rui Wang, Dan Zhang, Hao Song, Xiao-Yu Liu, Yong Qin. Enantioselective total synthesis of (+)-vincamine[J]. Chinese Chemical Letters,
;2022, 33(4): 2044-2046.
doi:
10.1016/j.cclet.2021.09.032
J.E. Saxton, The eburnamine–vincamine group, in: A. Weissberger, E. Taylor (Eds.), Indoles Part IV: The Monoterpene Indole Alkaloids, Wiley, New York, 1983, pp. 439–465.
Atta-ur-Rahman, M. SultanaS., Heterocycles 22 (1984) 841–858.
doi: 10.3987/R-1984-04-0841
M. Lounasmaa, A. Tolvanen, Eburnamine–vincamine alkaloids, in: G.A. Cordell (Ed. ), The Alkaloids: Chemistry and Pharmacology, Academic Press, New York, 1992, pp. 1–116.
J.E. Saxton, Nat. Prod. Rep. 11 (1994) 493–531.
J.E. Saxton, Nat. Prod. Rep. 13 (1996) 327–363.
J.E. Saxton, Nat. Prod. Rep. 14 (1997) 559–590.
doi: 10.1039/np9971400559
J. Leonard, Nat. Prod. Rep. 16 (1999) 319–338.
M.H. Zenk, M. Juenger, Phytochemistry 68 (2007) 2757–2772.
P. Cook, I. James, N. Engl. J. Med. 305 (1981) 1560–1564.
H.R. Olpe, G. Barrionuevo, G. Lynch, Life Sci. 31 (1982) 1947–1953.
Á. Vas, B. Gulyás, Med. Res. Rev. 25 (2005) 737–757.
doi: 10.1002/med.20043
A. Nemes, Monoterpenoid indole alkaloids, CNS and anticancer drugs, in J. Fischer, C.R. Ganellin (Eds. ), Analogue-Based Drug Discovery II, Wiley, Weinheim, 2010, pp. 189–215.
A.H.A. Fayed, Biol. Trace Elem. Res. 136 (2010) 314–319.
doi: 10.1007/s12011-009-8550-3
Y. Wang, Extraction, Separation, Purification, And Qualitative And Quantitative Analysis Of Vincamine in Vinca minor L, M.S. Thesis, Northwest University, 2009.
M.E. Kuehne, J. Am. Chem. Soc. 86 (1964) 2946.
doi: 10.1021/ja01068a044
K.H. Gibson, J.E. Saxton, J. Chem. Soc. D 799 (1969) 1490.
J.L. Herrmann, R.J. Cregge, J.E. Richman, C.L. Semmelhack, R.H. Schlessinger, J. Am. Chem. Soc. 96 (1974) 3702–3703.
doi: 10.1021/ja00818a083
K.H. Gibson, J.E. Saxton, Tetrahedron 33 (1977) 833–836.
J.L. Herrmann, R.J. Cregge, J.E. Richman, et al., J. Am. Chem. Soc. 101 (1979) 1540–1544.
doi: 10.1021/ja00500a028
D. Genin, R.Z. Andriamialisoa, N. Langlois, Y. Langlois, J. Org. Chem. 52 (1987) 353–356.
doi: 10.1021/jo00379a007
Z. Koblicová, J. Holubek, J. Trojánek, Collect. Czech. Chem. Commun. 53 (1988) 2722–2730.
doi: 10.1135/cccc19882722
M. Lounasmaa, A. Tolvanen, J. Org. Chem. 55 (1990) 4044–4047.
doi: 10.1021/jo00300a019
C. Szántay, L. Szabó, G. Kalaus, Tetrahedron Lett. 14 (1973) 191–192.
P. Pfäfi, W. Oppolzer, R. Wenger, H. Hauth, Helv. Chim. Acta. 58 (1975) 1131–1145.
W. Oppolzer, H. Hauth, P. Pfäfi, R. Wenger, Helv. Chim. Acta. 60 (1977) 1801–1810.
doi: 10.1002/hlca.19770600533
C. Szántay, L. Szabó, G. Kalaus, Tetrahedron 33 (1977) 1803–1808.
G. Rossey, A. Wick, E. Wenkert, J. Org. Chem. 47 (1982) 4745–4749.
doi: 10.1021/jo00145a028
L. Szabó, G. Kalaus, C. Szántay, Arch. Pharm. 316 (1983) 629–638.
doi: 10.1002/ardp.19833160709
L. Szabó, J. Sápi, G. Kalaus, et al., Tetrahedron 39 (1983) 3737–3747.
K. Hakam, M. Thielmann, T. Thielmann, E. Winterfeldt, Tetrahedron 43 (1987) 2035–2044.
P. Gmeiner, P.L. Feldman, M.Y. Chu-Moyer, H. Rapoport, J. Org. Chem. 55 (1990) 3068–3074.
doi: 10.1021/jo00297a023
D. Desmaële, K. Mekouar, J. d'Angelo, J. Org. Chem. 62 (1997) 3890–3901.
T. Nagy, L. Szabó, G. Kalaus, C. Szántay, Heterocycles 45 (1997) 2007–2013.
A.G. Schultz, W.P. Malachowski, Y. Pan, J. Org. Chem. 62 (1997) 1223–1229.
J.C.F. Alves, A.B.C. Simas, P.R.R. Costa, Tetrahedron 10 (1999) 297–306.
X. Wang, D. Xia, W. Qin, et al., Chem 2 (2017) 803–816.
L. Novák, J. Rohály, C. Szántay, L. Czibula, Heterocycles 6 (1977) 1149–1156.
P. Magnus, P. Brown, J. Chem. Soc. Chem. Commun. 4 (1985) 184–186.
M. Node, H. Nagasawa, K. Fuji, J. Am. Chem. Soc. 109 (1987) 7901–7903.
doi: 10.1021/ja00259a060
M. Node, H. Nagasawa, K. Fuji, J. Org. Chem. 55 (1990) 517–521.
doi: 10.1021/jo00289a025
A.G. Schultz, L. Pettus, J. Org. Chem. 62 (1997) 6855–6861.
D.S. Liyanage, C.S. Jungong, A.V. Novikov, Tetrahedron Lett. 56 (2015) 2269–2271.
K.R. Prasad, J.E. Nidhiry, Synlett 23 (2012) 1477–1480.
doi: 10.1055/s-0031-1291143
J.E. Nidhiry, K.R. Prasad, Tetrahedron 69 (2013) 5525–5536.
G. Pandey, A. Mishra, J. Khamrai, Org. Lett. 19 (2017) 3267–3270.
doi: 10.1021/acs.orglett.7b01410
C. Reimann, A. Ngamnithiporn, K. Hayashida, et al., Angew. Chem. Int. Ed. 60 (2021) 17957–17962.
doi: 10.1002/anie.202106184
M. Lounasmaa, E. Karvinen, Heterocycles 36 (1993) 751–760.
doi: 10.3987/COM-92-6220
D.B. England, A. Padwa, Org. Lett. 9 (2007) 3249–3252.
doi: 10.1021/ol071173x
D.B. England, A. Padwa, J. Org. Chem. 73 (2008) 2792–2802.
doi: 10.1021/jo8001003
M.W. Smith, R. Hunter, D.J. Patten, W. Hinz, Tetrahedron. Lett. 50 (2009) 6342–6346.
D.R. Bobeck, H.I. Lee, A.C. Flick, A. Padwa, J. Org. Chem. 74 (2009) 7389–7402.
doi: 10.1021/jo901336z
C. Piemontesi, Q. Wang, J. Zhu, Angew. Chem. Int. Ed. 55 (2016) 6556–6560.
doi: 10.1002/anie.201602374
P. Mondal, N.P. Argade, Org. Biomol. Chem. 14 (2016) 10394-10406.
doi: 10.1039/C6OB01438K
L. Salacz, C. Charpentier, J. Suffert, N. Girard, J. Org. Chem. 82 (2017) 2257–2262.
doi: 10.1021/acs.joc.6b02939
P. Mondal, N.P. Argade, Synthesis 49 (2017) 1849–1856.
Q. Zhou, X. Dai, H. Song, et al., Chem. Commun. 54 (2018), 9510–9512.
doi: 10.1039/c8cc05374j
B.M. Trost, Y. Bai, W.J. Bai, J.E. Schultz, J. Am. Chem. Soc. 141 (2019) 4811–4814.
doi: 10.1021/jacs.9b00788
G. Li, C. Piemontesi, Q. Wang, J. Zhu, Angew. Chem. Int. Ed. 58 (2019) 2870–2874.
doi: 10.1002/anie.201813920
W. Zhang, X. Chen, Y. An, et al., Chem. Eur. J. 26 (2020) 10439–10443.
doi: 10.1002/chem.202002404
D. Zhang, H. Song, Y. Qin, Acc. Chem. Res. 44 (2011) 447–457.
X.Y. Liu, Y. Qin, Acc. Chem. Res. 52 (2019) 1877–1891.
doi: 10.1021/acs.accounts.9b00246
X.Y. Liu, F.P. Wang, Y. Qin, Acc. Chem. Res. 54 (2021) 22–34.
doi: 10.1021/acs.accounts.0c00720
D. C. Behenna, Y. Liu, T. Yurino, et al., Nat. Chem. 4 (2012) 130–133.
doi: 10.1038/nchem.1222
B.M. Trost, Tetrahedron 71 (2015) 5708–5733.
A.Y. Hong, B.M. Stoltz, Eur. J. Org. Chem. 14 (2013) 2745–2759.
doi: 10.1002/ejoc.201201761
B.P. Pritchett, B.M. Stoltz, Nat. Prod. Rep. 35 (2018) 559–574.
O. Pamies, J. Margalef, S. Canellas, et al., Chem. Rev. 121 (2021) 4373-4505.
doi: 10.1021/acs.chemrev.0c00736
C. Xie, J. Luo, Y. Zhang, et al., Org. Lett. 20 (2018) 2386–2390.
doi: 10.1021/acs.orglett.8b00725
G. Barbe, A.B. Charette, J. Am. Chem. Soc. 130 (2008) 18–19.
doi: 10.1021/ja077463q
G. Pelletier, W.S. Bechara, A.B. Charette, J. Am. Chem. Soc. 132 (2010) 12817–12819.
doi: 10.1021/ja105194s
K.L. White, M. Mewald, M. Movassaghi, J. Org. Chem. 80 (2015) 7403–7411.
doi: 10.1021/acs.joc.5b01023
T. Kang, K.L. White, T.J. Mann, A.H. Hoveyda, M. Movassaghi, Angew. Chem. Int. Ed. 56 (2017) 13857–3860.
doi: 10.1002/anie.201708088
Y. Sasano, S. Nagasawa, M. Yamazaki, et al., Angew. Chem. Int. Ed. 53 (2014) 3236–3240.
doi: 10.1002/anie.201309634
Jingping Hu , Jing Xu . Total synthesis of a putative yuzurimine-type Daphniphyllum alkaloid C14–epi-deoxycalyciphylline H. Chinese Chemical Letters, 2024, 35(4): 108733-. doi: 10.1016/j.cclet.2023.108733
Peng Chen , Lijuan Liang , Yufei Zhu , Zhimin Xing , Zhenhua Jia , Teck-Peng Loh . Strategies for constructing seven-membered rings: Applications in natural product synthesis. Chinese Chemical Letters, 2024, 35(6): 109229-. doi: 10.1016/j.cclet.2023.109229
Tengfei Xuan , Xinyu Zhang , Wei Han , Yidong Huang , Weiwu Ren . Total synthesis of (+)-taberdicatine B and (+)-tabernabovine B. Chinese Chemical Letters, 2025, 36(2): 109816-. doi: 10.1016/j.cclet.2024.109816
Qunlong Zhang , Jingyi Kang , Jingwen Wang , Tiancheng Tan , Zhaoyong Lu . Divergent total synthesis of sesquiterpene (hydro)quinone meroterpenoids dysideanones A and E–G. Chinese Chemical Letters, 2025, 36(3): 109915-. doi: 10.1016/j.cclet.2024.109915
Zhenhao Wang , Yuliang Tang , Ruyu Li , Shuai Tian , Yu Tang , Dehai Li . Bioinspired synthesis of cochlearol B and ganocin A. Chinese Chemical Letters, 2024, 35(7): 109247-. doi: 10.1016/j.cclet.2023.109247
Xiao-Gang Wang , Ai-E Wang , Pei-Qiang Huang . Corrigendum to "A concise formal stereoselective total synthesis of (–)-swainsonine" [Chin Chem Lett 25 (2014) 193–196]. Chinese Chemical Letters, 2025, 36(3): 110597-. doi: 10.1016/j.cclet.2024.110597
Wei Zhou , Xi Chen , Lin Lu , Xian-Rong Song , Mu-Jia Luo , Qiang Xiao . Recent advances in electrocatalytic generation of indole-derived radical cations and their applications in organic synthesis. Chinese Chemical Letters, 2024, 35(4): 108902-. doi: 10.1016/j.cclet.2023.108902
Ke Zhang , Sheng Zuo , Pengyuan You , Tong Ru , Fen-Er Chen . Palladium-catalyzed stereoselective decarboxylative [4 + 2] cyclization of 2-methylidenetrimethylene carbonates with pyrrolidone-derived enones: Straightforward access to chiral tetrahydropyran-fused spiro-pyrrolidine-2,3-diones. Chinese Chemical Letters, 2024, 35(6): 109157-. doi: 10.1016/j.cclet.2023.109157
Hongjin Shi , Guoyin Yin , Xi Lu , Yangyang Li . Stereoselective synthesis of 2-deoxy-α-C-glycosides from glycals. Chinese Chemical Letters, 2024, 35(12): 109674-. doi: 10.1016/j.cclet.2024.109674
Ping Sun , Yuanqin Huang , Shunhong Chen , Xining Ma , Zhaokai Yang , Jian Wu . Indole derivatives as agrochemicals: An overview. Chinese Chemical Letters, 2024, 35(7): 109005-. doi: 10.1016/j.cclet.2023.109005
Zhenkang Ai , Hui Chen , Xuebin Liao . Nickel-catalyzed decarboxylative difluoromethylation and alkylation of alkenes. Chinese Chemical Letters, 2025, 36(3): 109954-. doi: 10.1016/j.cclet.2024.109954
Ao Sun , Zipeng Li , Shuchun Li , Xiangbao Meng , Zhongtang Li , Zhongjun Li . Stereoselective synthesis of α-3-deoxy-D-manno-oct-2-ulosonic acid (α-Kdo) derivatives using a C3-p-tolylthio-substituted Kdo fluoride donor. Chinese Chemical Letters, 2025, 36(3): 109972-. doi: 10.1016/j.cclet.2024.109972
Xiaoxia WANG , Ya'nan GUO , Feng SU , Chun HAN , Long SUN . Synthesis, structure, and electrocatalytic oxygen reduction reaction properties of metal antimony-based chalcogenide clusters. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1201-1208. doi: 10.11862/CJIC.20230478
Yihong Li , Zhong Qiu , Lei Huang , Shenghui Shen , Ping Liu , Haomiao Zhang , Feng Cao , Xinping He , Jun Zhang , Yang Xia , Xinqi Liang , Chen Wang , Wangjun Wan , Yongqi Zhang , Minghua Chen , Wenkui Zhang , Hui Huang , Yongping Gan , Xinhui Xia . Plasma enhanced reduction method for synthesis of reduced graphene oxide fiber/Si anode with improved performance. Chinese Chemical Letters, 2024, 35(11): 109510-. doi: 10.1016/j.cclet.2024.109510
Ting Xie , Xun He , Lang He , Kai Dong , Yongchao Yao , Zhengwei Cai , Xuwei Liu , Xiaoya Fan , Tengyue Li , Dongdong Zheng , Shengjun Sun , Luming Li , Wei Chu , Asmaa Farouk , Mohamed S. Hamdy , Chenggang Xu , Qingquan Kong , Xuping Sun . CoSe2 nanowire array enabled highly efficient electrocatalytic reduction of nitrate for ammonia synthesis. Chinese Chemical Letters, 2024, 35(11): 110005-. doi: 10.1016/j.cclet.2024.110005
Hong-Rui Li , Xia Kang , Rui Gao , Miao-Miao Shi , Bo Bi , Ze-Yu Chen , Jun-Min Yan . Interfacial interactions of Cu/MnOOH enhance ammonia synthesis from electrochemical nitrate reduction. Chinese Chemical Letters, 2025, 36(2): 109958-. doi: 10.1016/j.cclet.2024.109958
Jiaqi Ma , Lan Li , Yiming Zhang , Jinjie Qian , Xusheng Wang . Covalent organic frameworks: Synthesis, structures, characterizations and progress of photocatalytic reduction of CO2. Chinese Journal of Structural Chemistry, 2024, 43(12): 100466-100466. doi: 10.1016/j.cjsc.2024.100466
Yan-Li Li , Zhi-Ming Li , Kai-Kai Wang , Xiao-Long He . Beyond 1,4-addition of in-situ generated (aza-)quinone methides and indole imine methides. Chinese Chemical Letters, 2024, 35(7): 109322-. doi: 10.1016/j.cclet.2023.109322
Xiaoliu Liang , Chunliu Huang , Hui Liu , Hu Chen , Jiabao Shou , Hongwei Cheng , Gang Liu . Natural hydrogel dressings in wound care: Design, advances, and perspectives. Chinese Chemical Letters, 2024, 35(10): 109442-. doi: 10.1016/j.cclet.2023.109442
Yingjie Wang , Peng Tang , Wenchao Tu , Qi Gao , Cuizhu Wang , Luying Tan , Lixin Zhao , Hongye Han , Liefeng Ma , Kouharu Otsuki , Weilie Xiao , Wenli Wang , Jinping Liu , Yong Li , Zhajun Zhan , Wei Li , Xianli Zhou , Ning Li . Highly anticipated natural diterpenoids as an important source of new drugs in 2013–2023. Chinese Chemical Letters, 2025, 36(1): 109955-. doi: 10.1016/j.cclet.2024.109955