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8
A. Ekebergh, A. Börje and J. Mårtensson, Org. Lett., 2012, 14, 6274
(total synthesis).
cycloaddition reaction for the efficient synthesis of 1-
trifluoromethylated cyclopenta[b]indole alkaloids from -
trifluoromethyl 3-indolylmethanol silyl ethers (as all carbon 1,3-
dipoles) with ketene dithioacetals (as the two carbon push-pull
ethylene components). In this reaction the step-wise dehydrative
alkenylation of -trifluoromethyl-(indol-3-yl)methanols is the
crucial transformation. The [3+2] cycloaddition reaction can be
performed under very mild catalytic conditions and tolerate a
wide range of functional groups to give high to excellent yields of
10 products in most cases. Further studies are in progress.
Financial support of this research by the National Natural
Sciences Foundation of China (21072027, 21172030, 21272034
and 21202015) is greatly acknowledged.
DOI: 10.1039/C4CC05895J
Cheesman and S. Rosenzweig-Lipson, CNS Drug Rev., 2006, 12,
70
75
167; (b) K. A. Cunningham, N. C. Anastasio, R. G. Fox, S. J. Stutz,
M. J. Bubar, S. E. Swinford, C. S. Watson, S. R. Gilbertson, K. C.
Rice, S. Rosenzweig-Lipson and F. G. Moeller, ACS Chem.
Neurosci., 2013, 4, 110; (c) R. Neelamegam, T. Hellenbrand, F. A.
Schroeder, C. Wang and J. M. Hooker, J. Med. Chem., 2014, 57,
1488.
(a) L. Zhang, Y. Zhu, G. Yin, P. Lu and Y. Wang, J. Org. Chem.,
2012, 77, 9510; (b) Y. Lian and H. M. L. Davies, J. Am. Chem. Soc.,
2010, 132, 440; (c) B. Bajtos, M. Yu, H. Zhao and B. L. Pagenkopf,
J. Am. Chem. Soc., 2007, 129, 9631; (d) H. Xiong, H. Xu, S. Liao, Z.
Xie and Y. Tang, J. Am. Chem. Soc., 2013, 135, 7851; (e) J.
Barluenga, E. Tudela, A. Ballesteros and M. Tomas, J. Am. Chem.
Soc., 2009, 131, 2096; (f) H. Li, R. P. Hughes and J. Wu, J. Am.
Chem. Soc., 2014, 136, 6288.
5
9
80
Notes and references
10 B. Xu, Z.-L. Guo, W.-Y. Jin, Z.-P. Wang, Y.-G. Peng and Q.-X. Guo,
Angew. Chem., Int. Ed., 2012, 51, 1059.
15 1 (a) I. Ojima, Fluorine in Medicinal Chemistry and Chemical Biology,
Wiley-Blackwell, Oxford, U.K., 2009; (b) J. Wang, M. Sánchez-
Roselló, J. L. Aceña, C. del Pozo, A. E. Sorochinsky, S. Fustero, V.
A. Soloshonok and H. Liu, Chem. Rev., 2014, 114, 2432; (c) K.
Müller, C. Faeh and F. Diederich, Science, 2007, 317, 1881; (d) M.
85
11 -Trifluoromethyl- and -pentafluoroethyl-(indol-3-yl)methanols were
prepared by the nucleophilic addition of TMSCF3 or TMSC2F5 with
the corresponding indole-3-carbaldehydes. For details, see ESI.
12 (a) T. A. Hamlin, C. B. Kelly, R. M. Cywar and N. E. Leadbeater, J.
Org. Chem., 2014, 79, 1145; (b) R. J. Linderman and D. M. Graves,
J. Org. Chem., 1989, 54, 661; (c) C. B. Kelly, M. A. Mercadante, R.
J. Wiles and N. E. Leadbeater, Org. Lett., 2013, 15, 2222; (d) M. T.
Corbett, Q. Xu and J. S. Johnson, Org. Lett., 2014, 16, 2362; (e) G.
A. Olah and C. U. Pittman, Jr., J. Am. Chem. Soc., 1966, 88, 3310; (f)
H. Amouri, J.-P. Begue, A. Chennoufi, D. Bonnet-Delpon, M.
Gruselle and B. Malezieux, Org. Lett., 2000, 2, 807.
13 (a) D. Liang, M. Wang, B. Bekturhun, B. Xiong and Q. Liu, Adv.
Synth. Catal., 2010, 352, 1593; (b) H. Yuan, M. Wang, Y. Liu, L.
Wang, J. Liu and Q. Liu, Chem. Eur. J., 2010, 16, 13450; (c) H.
Yuan, M. Wang, Y. Liu and Q. Liu, Adv. Synth. Catal., 2009, 351,
112.
20
25
30
35
40
45
50
55
60
65
C. Walker and M. C. Y. Chang, Chem. Soc. Rev., 2014, 43, 6527.
For selected recent reviews, see: (a) T. Liang, C. N. Neumann and T.
Ritter, Angew. Chem., Int. Ed., 2013, 52, 8214; (b) L. Chu and F.-L.
Qing, Acc. Chem. Res. 2014, 47, 1513; (c) X. Liu, C. Xu, M. Wang
and Q. Liu, Chem. Rev. dx.doi.org/10.1021/cr400473a; (d) G. K. S.
Prakash and A. K. Yudin, Chem. Rev., 1997, 97, 757; (e) A. D.
Dilman and V. V. Levin, Eur. J. Org. Chem., 2011, 831; (f) C. B.
Kelly, M. A. Mercadantea and N. E. Leadbeater, Chem. Commun.,
2013, 49, 11133.
For reviews, see: (a) L. Pan, X. Bi and Q. Liu, Chem. Soc. Rev.,
2013, 42, 1251; (b) L. Pan and Q. Liu, Synlett, 2011, 1073; (c) Q.
Liu, 1,1-Bis(organosulfanyl)alk-1-enes (Ketene S,S-Acetals), Update
2014/2, in Science of Synthesis, Compounds with Four and Three
Carbon-Heteroatom Bonds, ed. M. B. Nielsen, N. Krause, I. Marek,
E. Schaumann and T. Wirth, Georg Thieme, Stuttgart, p. 245; (d) H.
Junjappa, H. Ila and C. V. Asokan, Tetrahedron, 1990, 46, 5423; (e)
R. K. Dieter, Tetrahedron, 1986, 42, 3029.
For selected recent reports, see: (a) N. Jung, B. Stanek, S. Gräßle, M.
Nieger and S. Bräse, Org. Lett., 2014, 16, 1112; (b) N. Jung, S.
Grässle, D. S. Lütjohann and S. Bräse, Org. Lett., 2014, 16, 1036; (c)
S. Yugandar, N. C. Misra, G. Parameshwarappa, K. Panda and H. Ila,
Org. Lett., 2013, 15, 5250; (d) Y. Dong, B. Liu, P. Chen, Q. Liu and
M. Wang, Angew. Chem., Int. Ed., 2014, 53, 3442; (e) T. Wu, L. Pan,
X. Xu and Q. Liu, Chem. Commun., 2014, 50, 1797; (f) Y. Liu, B.-D.
Barry, H. Yu, J. Liu, P. Liao and X. Bi, Org. Lett., 2013, 15, 2608;
(g) G. Fang, J. Li, Y. Wang, M. Gou, Q. Liu, X. Li and X. Bi, Org.
Lett., 2013, 15, 4126; (h) H. Yuan, Y. Zheng, Z. Fang, X. Bi and J.
Zhang, Green Chem., 2014, 16, 2653; (i) X. Liu, X. Xu, L. Pan, Q.
Zhang and Q. Liu, Org. Biomol. Chem., 2013, 11. 6703; (j) X. Liu, L.
Zhang, X. Xu, S. Wang, L. Pan, Q. Zhang and Q. Liu, Chem.
Commun., 2014, 50, 8764; (k) Y. Zhang, L. Pan, X. Xu, H. Luo and
Q. Liu, Chem. Commun., 2014, 50, 11039.
90
2
3
4
95
100
14 (a) A. Fu, W. Meng, H. Li, J. Nie and J.-A. Ma, Org. Biomol. Chem.,
2014, 12, 1908; (b) J. Nie, G.-W. Zhang, L. Wang, A. Fu, Y. Zheng
and J.-A. Ma, Chem. Commun., 2009, 2356.
105 15 V. K. Pandey and P. Anbarasan, J. Org. Chem., 2014, 79, 4154.
16 (a) B. M. Trost and D. M. T. Chen, J. Am. Chem. Soc., 1979, 101,
6429; (b) B. M. Trost, D. A. Bringley, T. Zhang and N. Cramer, J.
Am. Chem. Soc., 2013, 135, 16720.
5
6
(a) X. Liu, L. Pan, J. Dong, X. Xu, Q. Zhang and Q. Liu, Org. Lett.,
2013, 15, 6242; (b) C. Xu, J. Liu, W. Ming, Y. Liu, J. Liu, M. Wang
and Q. Liu, Chem. Eur. J., 2013, 19, 9104; (c) Z. Fang, J. Liu, Q. Liu
and X. Bi, Angew. Chem., Int. Ed., 2014, 53, 5039; (d) Z. Mao, F.
Huang, H. Yu, J. Chen, Z. Yu and Z. Xu, Chem. Eur. J., 2014, 20,
3439; (e) Q. Yang, P. Wu, J. Chen and Z. Yu, Chem. Commun.,
2014, 50, 6337.
(a) P. J. Proteau, W. H. Gerwick, F. Garcia-Pichel and R. Castenholz,
Experientia, 1993, 49, 825 (scytonemin structure determination); (b)
E. P. Balskus and C. T. Walsh, J. Am. Chem. Soc., 2008, 130, 15260;
(c) E. P. Balskus and C. T. Walsh, J. Am. Chem. Soc., 2009, 131,
14648 (biosynthesis of scytonemin). (d) C. P. Miller, P. Bhaket, N.
Muthukaman, C. R. Lyttle, M. Shomali, K. Gallacher, C. Slocum and
G. Hattersley, Bioorg. Med. Chem. Lett., 2010, 20, 7516.
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