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1643, 1545, 1498, 1264, 1076, 788; HRMS m/z (ESI) calcd for
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3-Cyanopropyl (8S,9S,10R,13S,14S,17S)-10,13-dimethyl-3-
oxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-
cyclopenta[a]phenanthrene-17-carboxylatee (2la). A colorless
1
oil (47.8 mg, 62%). H NMR (400 MHz, CDCl3) δ 5.71 (s, 1H),
4.25 – 4.08 (m, 2H), 2.45 (t, J = 7.2 Hz, 2H), 2.42 – 2.23 (m,
5H), 2.17 – 2.07 (m, 1H), 2.04 – 1.94 (m, 4H), 1.87 – 1.78 (m,
2H), 1.76 – 1.68 (m, 2H), 1.63 – 1.49 (m, 2H), 1.45 – 1.24 (m,
3H), 1.17 (s,3H), 1.13 – 0.91 (m, 3H), 0.70 (s, 3H); 13C NMR
(100 MHz, CDCl3) δ 199.5, 173.5, 171.0, 123.8, 118.7, 61.8,
55.2, 55.0, 53.6, 43.9, 38.5, 38.1, 35.6, 33.9, 32.7, 31.8, 24.8,
24.3, 23.5, 20.8, 17.3, 14.4, 13.5; ATR-FTIR (cm -1): 2246, 1730,
1673, 1615, 1451, 1229, 1163, 1051, 739; HRMS m/z (ESI)
calcd for C24H33NNaO3 (M + Na)+ 406.2353, found 406.2349.
3-Cyanopropyl
(E)-2-(5-fluoro-2-methyl-1-(4-
(methylsulfinyl)benzylidene)-1H-inden-3-yl)acetate (2ma) . A
1
yelow oil (47.6 mg, 55%). H NMR (400 MHz, CDCl3) δ 7.76 –
7.56 (m,4H), 7.18 – 7.12 (m, 2H), 6.87 (dd, J = 8.8, 2.4 Hz, 1H),
6.57 (td, J = 8.9, 2.4 Hz, 1H), 4.23 (t, J = 6.0 Hz, 2H), 3.59 (s
,2H), 2.81 (s, 3H), 2.37 (t, J = 7.1 Hz, 2H), 2.21 (s, 3H), 2.02 –
1.96 (m, 2H); 13C NMR (100 MHz, CDCl3) δ 169.9, 163.3 (d, J =
246.8 Hz), 146.5 (d, J = 8.8 Hz), 145.5, 141.5, 139.5, 138.3,
131.4, 130.2, 129.4, 128.5, 123.8, 118.7, 110.9 (d, J = 22.7 Hz),
105.9 (d, J = 23.9 Hz), 62.8, 43.9, 31.6, 24.7, 14.1, 10.6; 19F
NMR (376 MHz, CDCl3) δ -112.8; ATR-FTIR (cm -1): 2247,
1728, 1601, 1565, 1462, 1263, 1090, 805; HRMS m/z (ESI)
calcd for C24H22FNNaO3S (M + Na)+ 446.1197, found 446.1201..
3-Cyanopropyl 2-(1-(4-chlorobenzoyl)-5-methoxy-2-methyl-
1
1H-indol-3-yl)acetate (2na). A yelow oil (62.1 mg, 73%): H
NMR (400 MHz, CDCl3) δ 7.66 (d, J = 8.5 Hz, 2H), 7.47 (d, J =
8.5 Hz, 2H), 6.95 (d, J = 2.5 Hz, 1H), 6.86 (d, J = 9.0 Hz, 1H),
6.67 (dd, J = 9.0, 2.5 Hz, 1H), 4.22 (t, J = 6.0 Hz, 2H), 3.83 (s,
3H), 3.69 (s, 2H), 2.38 (s, 3H), 2.35 (t, J = 7.1 Hz, 2H), 2.01 –
1.94 (m, 2H); 13C NMR (100 MHz, CDCl3) δ 170.5, 168.2,
156.0, 139.2, 136.0, 133.7, 131.1, 130.7, 130.4, 129.1, 118.7,
114.9, 112.1, 111.5, 101.2, 62.6, 55.7, 30.1, 24.7, 14.1, 13.3;
ATR-FTIR (cm -1): 2246, 1737, 1681, 1552, 1478, 1385, 1321,
1089, 1035, 804, 754; HRMS m/z (ESI) calcd for
C23H21ClN2NaO4 (M + Na)+ 447.1082, found 447.1087.
Acknowledgments
We acknowledge the ‘‘1000-Youth Talents Plan’’ and the
‘‘Jiangsu Specially-Appointed Professor Plan’’, and thank the
NSF of China (Grant 2167020084), the Jiangsu Provincial Nature
Science Foundation (SBK2016021885), the Top-notch Academic
Programs Project of Jiangsu Higher Education Institutions, and
the Priority Academic Program Development of Jiangsu Higher
Education Institutions for financial support.
9. Nishimura, T.; Yoshinaka, T.; Nishiguchi, Y.; Maeda, Y.;
Uemura, S. Org. Lett. 2005, 7, 2425.
10. Zhao, B.; Shi, Z. Angew. Chem. Int. Ed. 2017, 56, 12727.
11. (a) Yang, H.-B.; Selander, N. Chem. Eur. J. 2017, 23, 1779. (b)
Yang, H.-B.; Pathipati, S. R.; Selander, N. ACS Catal. 2017, 7,
8441.
12. Li, L.-Y.; Chen, H.-G.; Mei, M.-J.; Zhou, L. Chem. Commun.
2017, 53, 11544.
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