Organic Letters
Letter
X.-Y.; Shi, M. Org. Chem. Front. 2015, 2, 1516−1520. (d) Fu, L.;
Davies, H. M. L. Org. Lett. 2017, 19, 1504−1507.
ACKNOWLEDGMENTS
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We thank DST-SERB (EMR/2016/003677) for the financial
support. S.R. thanks CSIR, New Delhi, for the fellowship. We
also thank DST-FIST for the ESI-MS facility and Mr.
Ramkumar, IIT Madras, for single-crystal X-ray analysis.
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(13) (a) Sanchez-Rosello, M.; Acena, J. L.; Simon-Fuentes, A.; del
̃
Pozo, C. Chem. Soc. Rev. 2014, 43, 7430−7453. (b) Enders, D.; Wang,
C.; Liebich, J. X. Chem. - Eur. J. 2009, 15, 11058−11076.
(14) (a) Miyaji, R.; Asano, K.; Matsubara, S. Org. Lett. 2013, 15,
3658−3661. (b) Du, J.-Y.; Zeng, C.; Han, X.-J.; Qu, H.; Zhao, X.-H.;
An, X.-T.; Fan, C.-A. J. Am. Chem. Soc. 2015, 137, 4267−4273.
(c) Xiao, X.; Liu, X.; Dong, S.; Cai, Y.; Lin, L.; Feng, X. Chem. - Eur. J.
2012, 18, 15922−15926. (d) Gu, Q.; You, S.-L. Chem. Sci. 2011, 2,
1519−1522. (e) Liu, X.; Lu, Y. Org. Lett. 2010, 12, 5592−5595.
(f) Roy, T. K.; Parhi, B.; Ghorai, P. Angew. Chem., Int. Ed. 2018, 57,
9397−9401.
(15) (a) Sydorenko, N.; Zificsak, C. A.; Gerasyuto, A. I.; Hsung, R.
P. Org. Biomol. Chem. 2005, 3, 2140−2144. (b) Itoh, T.; Yokoya, M.;
Miyauchi, K.; Nagata, K.; Ohsawa, A. Org. Lett. 2003, 5, 4301−4304.
(c) Itoh, T.; Yokoya, M.; Miyauchi, K.; Nagata, K.; Ohsawa, A. Org.
Lett. 2006, 8, 1533−1535.
REFERENCES
■
(1) Fattorusso, E.; Taglialatela-Scafati, O. Modern Alkaloids:
Structure, Isolation, Synthesis, and Biology; Wiley, 2008.
(2) (a) Antkiewicz-Michaluk, L.; Rommelspacher, H. Current Topics
In Neurotoxicity: Isoquinolines and Beta-Carbolines As Neurotoxins and
Neuroprotectants: New Vistas In Parkinson’s Disease Therapy; Springer,
2012. (b) Cao, R.; Peng, W.; Wang, Z.; Xu, A. Curr. Med. Chem. 2007,
14, 479−500. (c) Laine, E. A.; Lood, C.; Koskinen, M. A. Molecules
2014, 19, 1544−1567. (d) Cain, M.; Weber, R. W.; Guzman, F.;
Cook, J. M.; Barker, S. A.; Rice, K. C.; Crawley, J. N.; Paul, S. M.;
Skolnick, P. J. Med. Chem. 1982, 25, 1081−1091.
(16) (a) Angenot, L.; Diberg, O.; Dupont, L. Tetrahedron Lett. 1975,
16, 1357−1358. (b) Verpoorte, R. J. Nat. Prod. 1986, 49, 1−25.
(c) Chbani, M.; Païs, M.; Delauneux, J.-M.; Debitus, C. J. Nat. Prod.
1993, 56, 99−104.
(3) (a) Cox, E. D.; Cook, J. M. Chem. Rev. 1995, 95, 1797−1842.
́
́
(b) Milen, M.; Abranyi-Balogh, P. Chem. Heterocycl. Compd. 2016, 52,
996−998.
(4) (a) Taylor, M. S.; Jacobsen, E. N. J. Am. Chem. Soc. 2004, 126,
10558−10559. (b) Raheem, I. T.; Thiara, P. S.; Peterson, E. A.;
Jacobsen, E. N. J. Am. Chem. Soc. 2007, 129, 13404−13405.
(c) Larghi, E. L.; Amongero, M.; Bracca, A. B. J.; Kaufman, T. S.
̈
ARKIVOC 2005, 98−153. (d) Stockigt, J.; Antonchick, A. P.; Wu, F.;
Waldmann, H. Angew. Chem., Int. Ed. 2011, 50, 8538−8564.
(e) Dalpozzo, R. Molecules 2016, 21, 699.
(5) (a) Tietze, L. F. Chem. Rev. 1996, 96, 115−136. (b) Nicolaou, K.
C.; Edmonds, D. J.; Bulger, P. G. Angew. Chem., Int. Ed. 2006, 45,
7134−7186. (c) Shindoh, N.; Takemoto, Y.; Takasu, K. Chem. - Eur.
J. 2009, 15, 12168−12179.
(6) (a) Grondal, C.; Jeanty, M.; Enders, D. Nat. Chem. 2010, 2, 167.
(b) Volla, C. M. R.; Atodiresei, I.; Rueping, M. Chem. Rev. 2014, 114,
2390−2431. (c) Zhou, J. Chem. - Asian J. 2010, 5, 422−434.
(7) Albrecht, Ł.; Jiang, H.; Jørgensen, K. A. Angew. Chem., Int. Ed.
2011, 50, 8492−8509.
(8) (a) Du, Z.; Shao, Z. Chem. Soc. Rev. 2013, 42, 1337−1378.
(b) Deng, Y.; Kumar, S.; Wang, H. Chem. Commun. 2014, 50, 4272−
4284. (c) Inamdar, S. M.; Shinde, V. S.; Patil, N. T. Org. Biomol.
Chem. 2015, 13, 8116−8162. (d) Rueping, M.; Koenigs, R. M.;
Atodiresei, I. Chem. - Eur. J. 2010, 16, 9350−9365. (e) Zhong, C.; Shi,
X. Eur. J. Org. Chem. 2010, 2010, 2999−3025.
(9) (a) Qiu, H.; Li, M.; Jiang, L.-Q.; Lv, F.-P.; Zan, L.; Zhai, C.-W.;
Doyle, M. P.; Hu, W.-H. Nat. Chem. 2012, 4, 733−738. (b) Jiang, J.;
Xu, H.-D.; Xi, J.-B.; Ren, B.-Y.; Lv, F.-P.; Guo, X.; Jiang, L.-Q.; Zhang,
Z.-Y.; Hu, W.-H. J. Am. Chem. Soc. 2011, 133, 8428−8431. (c) Chen,
D.-F.; Zhao, F.; Hu, Y.; Gong, L.-Z. Angew. Chem., Int. Ed. 2014, 53,
10763−10767. (d) Jia, S.; Xing, D.; Zhang, D.; Hu, W. Angew. Chem.,
Int. Ed. 2014, 53, 13098−13101. (e) Zhang, D.; Zhou, J.; Xia, F.;
Kang, Z.; Hu, W. Nat. Commun. 2015, 6, 5801.
(10) (a) Chattopadhyay, B.; Gevorgyan, V. Angew. Chem., Int. Ed.
2012, 51, 862−872. (b) Davies, H. M. L.; Alford, J. S. Chem. Soc. Rev.
2014, 43, 5151−5162. (c) Anbarasan, P.; Yadagiri, D.; Rajasekar, S.
Synthesis 2014, 46, 3004−3023. (d) Wang, Y.; Lei, X.; Tang, Y. Synlett
2015, 26, 2051−2059. (e) Jiang, Y.; Sun, R.; Tang, X.-Y.; Shi, M.
Chem. - Eur. J. 2016, 22, 17910−17924. (f) Li, Y.; Yang, H.; Zhai, H.
Chem. − Eur. J. 2018, 24, 12757−12766.
(11) (a) Yadagiri, D.; Chaitanya, M.; Reddy, A. C. S.; Anbarasan, P.
Org. Lett. 2018, 20, 3762−3765. (b) Yadagiri, D.; Reddy, A. C. S.;
Anbarasan, P. Chem. Sci. 2016, 7, 5934−5938. (c) Yadagiri, D.;
Anbarasan, P. Chem. Sci. 2015, 6, 5847−5852. (d) Rajasekar, S.;
Yadagiri, D.; Anbarasan, P. Chem. - Eur. J. 2015, 21, 17079−17084.
(e) Yadagiri, D.; Anbarasan, P. Chem. - Eur. J. 2013, 19, 15115−
15119. (f) Rajasekar, S.; Anbarasan, P. J. Org. Chem. 2014, 79, 8428−
8434. (g) Yadagiri, D.; Anbarasan, P. Org. Lett. 2014, 16, 2510−2513.
(12) (a) Alford, J. S.; Davies, H. M. L. J. Am. Chem. Soc. 2014, 136,
10266−10269. (b) Yang, J.-M.; Zhu, C.-Z.; Tang, X.-Y.; Shi, M.
Angew. Chem., Int. Ed. 2014, 53, 5142−5146. (c) Zhang, Y.-S.; Tang,
E
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