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. Author manuscript; available in PMC: 2012 Aug 5.
Published in final edited form as: Org Lett. 2011 Jul 12;13(15):3920–3923. doi: 10.1021/ol201443k

Table 1.

1H NMR Data (500 MHz) for Briareolate Esters 13

position 1 a (J in Hz) 2 b (J in Hz) 3 b (J in Hz)
2 5.50, br d (8.0)c 5.51, br d (7.5) 4.98, d (9.5)
2.48, dd (16.5, 11.0) 2.48, dd (16.0, 11.0) 2.13, m
1.26, m 1.26, m
2.29, m 2.35, m 2.22, m
2.17, m 2.22, m 1.38, m
6 6.21, br s 6.13, br s 5.62, d (9.0)
7 7.68, br s 7.64, br s 5.96, d (9.5)
10 3.80, d (11.5) 3.70, d (11.0) 3.68, d (12.0)
11 2.28, m 2.15, m 2.26, m
12 3.77, br q (3.0) 4.82, br q (3.0) 5.13, m
13α 2.07, dt (16.0, 3.0) 2.18, dt (13.0, 3.0) 2.10, m
13β 1.89, dt (16.0, 3.0) 1.87, dt (13.0, 3.0) 2.10, m
14 4.81, br s 5.08, br s 4.92, t (3.0)
15 0.87, s 0.87, s 1.42, m
16 1.73, s 1.75, s 1.38, m
17 3.52, q (6.0) 3.51, q (6.5) 3.76, q (7.0)
18 1.24, d (7.0) 1.28, d (7.0) 1.36, d (7.0)
20 0.89, d (7.0) 0.78, d (7.0) 0.89, d (7.0)
OCH3 3.60, s 3.69, s 3.87, s
C-2 ester 2.20, m 2.22, m 2.20, m
1.60, sextet (8.0) 1.64, m 1.61, m
0.93, t (7.0) 0.93, t (7.0) 0.96, t (7.0)
C-12 ester 2.28, m 2.32, m
1.62, m 1.69, m
1.33, m 1.34, m
1.33, m 1.34, m
0.89, t (7.0) 0.93, t (7.0)
C-14 ester 2.00, s 2.04, s 1.98, s
a

Measured in CD3OD,

b

Measured in CDCl3.