9
94
Synlett
A. Briš et al.
Letter
2
1
References and Notes
4.09 (t, J = 4.1 Hz, 2 H, 3 - =CCH ), 4.11–4.15 (m, 1 H, 17 -CH ),
2
2
1
1
6
(
.77, 6.79 (s, 1 H, 15 -CH), 7.01 (t, J = 4.1 Hz, 1 H, 3 - =CH), 7.09
t, J = 4.1 Hz, 1 H, 3 - =CH), 9.12, 9.14 (s, 1 H, 20-CH), 9.21, 9.24
s, 1 H, 5-CH), 9.78 (s, 1 H, 10-CH).
Compound 5: H NMR (300 MHz, CDCl ): δ = –1.79 (s, 1 H, NH),
1.59 (br. s, 1 H, NH), 1.69 (t, J = 6.6 Hz, 3 H, 8 -CH ), 1.71 (d,
J = 7.3 Hz, 3 H, 18 -CH ), 1.76–1.84 (m, 1 H, 17-CH ), 2.11–2.17
(1) Pandey, R. K.; Bellnier, D. A.; Smith, K. M.; Dougherty, T. J. Photo-
1
chem. Photobiol. 1991, 53, 65.
(
(
(
2) Sternberg, E. D.; Dolphin, D. Tetrahedron 1998, 54, 4151.
3) Zhang, J.; Deng, L.; Yao, J.; Gu, P.; Yang, F.; Wang, X.; Liu, W.;
Zhang, Y.; Ke, X.; Jing, X.; Chen, J. Bioorg. Med. Chem. 2011, 11,
1
3
2
–
3
1
3
2
5
520; and references cited therein.
4) (a) Kearns, P.; Margetić, D.; Warrener, R. N. Synlett 2014, 25,
601. (b) Trošelj, P.; Margetić, D.; Đilović, I.; Matković-
(
1
m, 1 H, 17-CH ), 2.18–2.25 (m, 1 H, 17-CH ), 2.46–2.55 (m, 1 H,
2
2
(
7-CH ), 3.31 (s, 3 H, 7-CH ), 3.48 (s, 3 H, 12-CH ), 3.53 (s, 3 H,
2 3 3
-CH ), 3.59 (s, 3 H, 15-OCH ), 3.73 (s, 3 H, 17-OCH ), 3.78 (q,
J = 6.6 Hz, 2 H, 8 -CH ), 4.37 (dd, J = 10.4, 2.3 Hz, 1 H, 17-CH),
.45 (q, J = 7.3 Hz, 1 H, 18-CH), 4.85 (dd, J = 15.3, 4.9 Hz, 1 H,
1
2
3
3
3
Čalogović, D. J. Heterocycl. Chem. 2013, 50, 83.
1
2
(
5) (a) Margetić, D. Curr. Org. Chem. 2012, 16, 829. (b) Tang, H.;
Merican, Z.; Dong, Z.; Margetić, D.; Marinić, Ž.; Gunter, M. J.;
Officer, D.; Butler, D. N.; Warrener, R. N. Tetrahedron Lett. 2009,
4
1
2
2
3 -CH ), 5.04 (dd, J = 15.3, 4.9 Hz, 1 H, 13 -CH ), 5.26 (d,
2
2
1
1
J = 18.8 Hz, 1 H, 15 -CH ), 5.52 (d, J = 18.8 Hz, 1 H, 15 -CH ),
2
2
50, 667. (c) Margetić, D.; Mann, D. A.; Warrener, R. N. ARKIVOC
2
6
1
6
7
1
1
.14 (dd, J = 11.6, 1.1 Hz, 1 H, 3 -C=CH ), 6.35 (dd, J = 11.6,
.1 Hz, 1 H, 3 -C=CH ), 6.42 (dd, J = 3.3, 1.8 Hz, 1 H, 13 -ArH),
.49 (d, J = 2.9 Hz, 1 H, 13 -ArH), 6.75 (t, J = 5.3 Hz, 1 H, 13 -NH),
.49 (dd, J = 1.8, 0.8 Hz, 1 H, 13 -ArH), 8.08 (dd, J = 18.1, 11.5 Hz,
2
2014, (xv), 210.
2
2
2
(
(
(
6) (a) Mao, H.-J.; Chen, Z.-L.; Ye, Y. Adv. Mater. Res. 2012, 393-395,
7
2
1029. (b) Yan, Y.-J.; Zheng, M.-Z.; Chen, Z.-L. Bioorg. Med. Chem.
8
2010, 18, 6282.
1
H, 3 -CH=), 8.79 (s, 1 H, 20-H), 9.62 (s, 1 H, 5-H), 9.68 (s, 1 H,
7) Yao, J.; Zhang, W.; Sheng, C.; Miao, Z.; Yang, F.; Yu, J.; Zhang, L.;
0-H).
Song, Y.; Zhou, T.; Zhou, Y. Bioorg. Med. Chem. Lett. 2008, 18,
(
9) Haner, J.; Kelsey, J.; Menard, M. L.; Howel, J.; Nagireddy, J.;
293.
Raheem, M. A.; Tam, W. Synthesis 2012, 44, 2713.
8) All novel compounds gave satisfactory 1H, 13C NMR, and high-
resolution mass spectra.
(
10) Winling, A.; Russell, R. A. J. Chem. Soc., Perkin Trans. 1 1998,
921.
11) Hong, V.; Kislukhin, A. A.; Finn, M. G. J. Am. Chem. Soc. 2009,
31, 9986.
(12) Warrener, R. N.; Butler, D. N.; Margetić, D. Aust. J. Chem. 2003,
56, 811.
(13) Margetić, D.; Warrener, R. N. J. Heterocycl. Chem. 2014, 51, 1369.
(14) Uchoa, A. F.; de Oliveira, K. T.; Baptista, M. S.; Bortoluzzi, A. J.;
Iamamoto, Y.; Serra, O. A. J. Org. Chem. 2011, 76, 8824.
3
1
Representative H NMR spectroscopic data:
(
1
Compound 3: Obtained as a 1:1 mixture of 2-epimers. H NMR
1
(
300 MHz, CDCl ): δ = –1.81, –1.76 (s, 1 H, NH), –0.98, –0.92 (s,
3
2
1
1
H, NH), 1.78 (t, J = 7.5 Hz, 3 H, 8 -CH ), 2.36, 2.39 (s, 3 H, 18 -
3
2
CH ), 2.93–3.01 (m, 1 H, 17-CH ), 3.04–3.11 (m, 1 H, 17 -CH ),
3
2
2
3
1
3
5
.41 (s, 3 H, 7-CH ), 3.46, 3.47 (s, 3 H, 2-CH ), 3.70. 3.71 (s, 3 H,
3
3
2-CH ), 3.74, 3.75 (s, 3 H, OCH ), 3.79 (s, 3 H, OCH ), 3.86 (s,
3
3
3
1
H, OCH ), 3.91 (q, J = 7.5 Hz, 2 H, 8 -CH ), 3.96 (dd, J = 13.9,
3
2
1
1
.1 Hz, 1 H, 17 -CH ), 4.05 (dd, J = 9.5, 3.1 Hz, 1 H, 17 -CH ),
2
2
©
Georg Thieme Verlag Stuttgart · New York — Synlett 2015, 26, 991–994