omphadiol (0.35Hz/4)


Gaussian numbering
1H-1H Js
 -ppm- -#-   H13   H19   H20   H21   H22   H23   H24   H25   H26   H27   H28   H29   H30   H31   H32   H33   H34   H35   H36   H37   H38   H39   H40   H41   H42   H43   
  1.64 H13
  1.76 H19   9.9
  0.62 H20    -     - 
  3.26 H21    -     -    8.3
  1.58 H22    -   11.9    -     - 
  1.52 H23    -    2.6    -     -  -14.2
  1.79 H24    -    0.8    -     -     -     - 
  1.43 H25    -     -     -     -     -     -  -12.8
  2.10 H26  11.4    -     -     -     -     -   12.3   8.0
  1.81 H27   3.8    -     -     -     -     -    9.2   0.8 -12.8
  0.78 H28    -     -    8.4    -     -     -     -     -     -     - 
  0.35 H29    -     -    5.1    -     -     -     -     -     -     -   -5.2
 -0.49 H30    -    1.1    -     -     -     -     -     -     -     -     -     - 
  1.26 H31    -     -     -     -     -     -     -     -     -     -     -     -     - 
  1.26 H32    -     -     -     -     -     -     -     -     -     -     -     -     -     - 
  1.26 H33    -     -     -     -     -     -     -     -     -     -     -     -     -     -     - 
  0.71 H34    -     -     -    1.0    -     -     -     -     -     -     -     -     -     -     -     - 
  1.07 H35    -     -     -     -     -     -     -     -     -     -     -    0.7    -     -     -     -     - 
  1.07 H36    -     -     -     -     -     -     -     -     -     -     -    0.7    -     -     -     -     -     - 
  1.07 H37    -     -     -     -     -     -     -     -     -     -     -    0.7    -     -     -     -     -     -     - 
  0.94 H38    -     -     -     -     -     -     -     -     -     -     -     -     -     -     -     -     -     -     -     - 
  0.94 H39    -     -     -     -     -     -     -     -     -     -     -     -     -     -     -     -     -     -     -     -     - 
  0.94 H40    -     -     -     -     -     -     -     -     -     -     -     -     -     -     -     -     -     -     -     -     -     - 
  1.10 H41    -     -     -     -    0.8    -     -     -     -     -     -     -     -     -     -     -     -     -     -     -     -     -     - 
  1.10 H42    -     -     -     -    0.8    -     -     -     -     -     -     -     -     -     -     -     -     -     -     -     -     -     -     - 
  1.10 H43    -     -     -     -    0.8    -     -     -     -     -     -     -     -     -     -     -     -     -     -     -     -     -     -     -     - 

13C-1H Js
 -ppm- -#-   H13   H19   H20   H21   H22   H23   H24   H25   H26   H27   H28   H29   H30   H31   H32   H33   H34   H35   H36   H37   H38   H39   H40   H41   H42   H43   
 47.66 C1   -4.0 124.5    -     -   -4.4  -4.0    -    5.5   1.8   2.1   0.8    -     -    3.2   3.2   3.2    -     -     -     -    0.6   0.6   0.6    -     -     - 
 50.19 C2  131.1  -4.2   1.8    -    3.2   9.0    -    6.3  -3.6  -3.0   2.7   4.8    -     -     -     -     -    3.0   3.0   3.0    -     -     -     -     -     - 
 20.67 C3   -4.6   5.1  -2.6    -     -     -     -     -    3.7   5.7  -2.2  -1.9    -     -     -     -     -   -4.3  -4.3  -4.3    -     -     -     -     -     - 
 28.79 C4    0.7    -  157.4  -4.1    -     -     -     -     -     -   -2.4  -3.0    -     -     -     -     -    4.6   4.6   4.6    -     -     -     -     -     - 
 80.43 C5     -     -   -3.2 139.6   2.3  10.0    -     -     -     -    2.5   5.8    -     -     -     -     -     -     -     -    3.7   3.7   3.7   3.5   3.5   3.5
 40.11 C6     -    2.1   0.7    -   -3.5  -4.1    -     -     -     -     -     -     -     -     -     -     -     -     -     -   -3.2  -3.2  -3.2  -3.6  -3.6  -3.6
 39.79 C7    4.3  -4.2    -    1.9 128.7 124.1    -    0.9    -     -     -     -     -     -     -     -     -     -     -     -    4.8   4.8   4.8   4.1   4.1   4.1
 80.51 C8     -   -2.2    -     -    1.6   2.1  -1.7  -4.1    -    6.4    -     -     -   -3.8  -3.8  -3.8    -     -     -     -     -     -     -     -     -     - 
 42.87 C9    2.4   0.6    -     -     -     -  125.1 129.4  -4.1  -3.1    -     -     -    3.7   3.7   3.7    -     -     -     -     -     -     -     -     -     - 
 23.24 C10  -4.2    -     -     -     -     -   -3.9  -2.2 131.2 131.9    -     -     -     -     -     -     -     -     -     -     -     -     -     -     -     - 
 22.86 C11   3.8    -   -2.7   3.9    -     -     -     -     -     -  155.3 154.4    -     -     -     -     -    4.6   4.6   4.6    -     -     -     -     -     - 
 23.80 C14    -    2.2    -     -     -     -    1.7   1.0    -     -     -     -     -  126.0 126.0 126.0    -     -     -     -     -     -     -     -     -     - 
 17.52 C16   5.0    -    5.7    -     -     -     -     -     -     -    4.7   2.5    -     -     -     -     -  126.4 126.4 126.4    -     -     -     -     -     - 
 26.02 C17    -     -     -    1.8   3.0   2.6    -     -     -     -     -     -     -     -     -     -     -     -     -     -  125.8 125.8 125.8   5.2   5.2   5.2
 16.55 C18    -     -     -    4.6   6.7   2.4    -     -     -     -     -     -     -     -     -     -     -     -     -     -    4.4   4.4   4.4 126.7 126.7 126.7
 -ppm- -#-   H13   H19   H20   H21   H22   H23   H24   H25   H26   H27   H28   H29   H30   H31   H32   H33   H34   H35   H36   H37   H38   H39   H40   H41   H42   H43   
1H data (JH-H abs sorted)

3.26 (8.3, 1.0)
2.10 (12.8, 12.3, 11.4, 8.0)
1.81 (12.8, 9.2, 3.8, 0.8)
1.79 (12.8, 12.3, 9.2, 0.8)
1.76 (11.9, 9.9, 2.6, 0.8)
1.64 (11.4, 9.9, 3.8)
1.58 (14.2, 11.9, 0.8, 0.8)
1.52 (14.2, 2.6)
1.43 (12.8, 8.0, 0.8)
1.26
1.10 (0.8)
1.07 (0.7)
0.94
0.78 (8.4, 5.2)
0.71 (1.0)
0.62 (8.4, 8.3, 5.1)
0.35 (5.2, 5.1, 0.7, 0.7)
-0.49 (1.1)
13C data
  8  80.5 (6.4, -4.1, -3.8, -3.8)
  5  80.4 (139.6, 10.0, 5.8, 3.7)
  2  50.2 (131.1, 9.0, 6.3, 4.8)
  1  47.7 (124.5, 5.5, -4.4, -4.0)
  9  42.9 (129.4, 125.1, -4.1, 3.7)
  6  40.1 (-4.1, -3.6, -3.6, -3.6)
  7  39.8 (128.7, 124.1, 4.8, 4.8)
  4  28.8 (157.4, 4.6, 4.6, 4.6)
 17  26.0 (125.8, 125.8, 125.8, 5.2)
 14  23.8 (126.0, 126.0, 126.0, 2.2)
 10  23.2 (131.9, 131.2, -4.2, -3.9)
 11  22.9 (155.3, 154.4, 4.6, 4.6)
  3  20.7 (5.7, 5.1, -4.6, -4.3)
 16  17.5 (126.4, 126.4, 126.4, 5.7)
 18  16.5 (126.7, 126.7, 126.7, 6.7)

[ Notes ]
  • Kalesse's paper has comparison with the original natural product and two more synthetic omphadiols
  • Zhou et. al. JOC 2014 5345 has several incorrect constants listed:
    • H7beta 1.42ppm (t 3.5Hz) - H7beta is anti to H8: Jcalcd=11.9Hz; also: the geminal Jcalcd=14.2Hz
    • H11beta 1.79ppm (ddd 18.1 10.5 5.0) - there should not be such a large (18.1Hz) constant anywhere in this structure