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. Author manuscript; available in PMC: 2012 Oct 28.
Published in final edited form as: J Nat Prod. 2011 Sep 14;74(10):2273–2277. doi: 10.1021/np2003066

Table 1.

1H and 13C NMR Data for Berkeleyones A-C, 4, 5, 7(CDCl3)a

berkeleyone A, 4 berkeleyone B, 5 berkeleyone C, 7
no. δC multd δH (J in Hz)c δC, mult.d δH (J in Hz)c δC, mult.d δH (J in Hz)c
1 78.2, CH 3.07, dd (11.3, 4.2) b178.2, C 177.4, C
2 26.8, CH2 1.50, m 29.7, CH2 α 1.80, m
β 1.90, m
29.1, CH2 α 2.00, m
β 1.80, m
3 38.4, CH2 α 1.57, m
β 0.61, m
33.7, CH2 α 2.25, m
β 1.40, m
33.3, CH2 1.6, m
4 37.7, C 43.0, C 40.8, C
5 52.7, CH 0.49, m 43.8, CH 0.85, dd (12.5, 2.0) 41.0, CH 1.00, dd (13.5, 3.4)
6 39.0, CH2 α 1.60, m
β 1.90, dd (13.2, 3.0)
41.4, CH2 α 1.70, t (13.2)
β 2.00, m
41.2, CH2 α 1.70, m
β 2.00, m
7 51.0, C 51.2, C 51.2, C
8 207.9, C 207.4, C 207.5, C
9 79.9, C 80.0, C 80.3, C
10 204.1, C 204.0, C 204.0, C
11 72.5, C 71.8, C 71.8, C
12 47.9, C 45.9, C 46.2, C
13 32.9, CH2 α 2.18, dt (13.7, 3.5)
β 2.00, td (13.7, 3.7)
31.2, CH2 α 2.62, bd (17.6, 2.1)
β 2.44, dd (17.6, 7.1)
31.1, CH2 α 2.71, bd (18.2)
β 2.45, dd (18.2, 6.7)
14 18.2, CH2 α 1.40, m
β 1.60, m
123.9, CH 5.70, dd (7.1, 2.1) 125.5, CH 5.59, dd (6.7, 2.3)
15 54.7, CH 0.49, m 144.5, C 142.4, C
16 38.7, C 75.9, C 145.4, C
17 27.8, CH3 0.92, s 35.5, CH3 1.40, s 26.4, CH3 1.81, s
18 15.5, CH3 0.71, s 33.8, CH3 1.36, s 114.9, CH2 4.86, bs
4.60, bs
19 17.2, CH3 1.19, s 15.5, CH3 1.18, s 16.3, CH3 1.22, s
20 168.6, C 168.6, C 168.5, C
21 15.2, CH3 1.36, s 15.0, CH3 1.31, s 15.0, CH3 1.33, s
22 145.6, C 145.4, C 145.7, C
23 112.4, CH2 5.34, bs
4.83, bs
112.4, CH2 5.39, bs
4.87, bs
112.4, CH2 5.39, bs
4.88, bs
24 22.1, CH3 1.44, s 22.4, CH3 1.49, s 22.5, CH3 1.48, s
25 15.8, CH3 0.76, s 21.4, CH3 1.18, s 22.4, CH3 0.93, s
OCH3 52.5, CH3 3.70, s 52.6, CH3 3.71, s 52.6, CH3 3.72, s
a

All assignments are based on COSY, NOE, HSQC and HMBC experiments.

b

Required longer D1.

c

300 MHz for 1H NMR, HMBC

d

75 MHz for 13C NMR.