From Plant to Patient: Thapsigargin, a Tool for Understanding …
69
Fig. 6 Slovanolides isolated
from fruits of T. garganica
[54, 57]
1 1
5 5 6 6 7 7
8 8
9 9
10 10
2 2
3 3
4 4
O
12 12
11 11
15 15
O
14 14
O
13 13
O
R
2
O
O
O
R
1
R 3
39 R
1 = 2-MeBut, R 2 = CH 3 (CH 2 ) 2 CO, R 3 = H
40 R
1 = iVal,
R 2 = 2-MeBut,
R 3 = H
41 R 1 = CH 3 CO, R 2 = 2-MeBut,
R 3 = CH 3 CO
42 R
1 = CH 3 CO, R 2 = 2-Sen,
R 3 = CH 3 CO [54]
43 R
1 = H,
R 2 = 2-MeBut,
R 3 = C H 3 CO [54]
44 R
1 = CH 3 CO, R 2 = 2-Sen,
R 3 = CH 3 CO [54]
[54, 57]
[54]
[54]
O
O
O
O
O
O
O
R
1
H
O
R
O
O
O
O
R 1
O
O
H
O
O
OH
O
OH
R
1 OH
45
O
R
OH
Scheme 4 Rearrangements of 11-hydroxyslovanolides to give 1,5-dimethylazulene (45)
O
O
O
O
O
O
O
R
1
O
R
O
HO
O
O
O
O
O
O
R
1
O
R
O
O
O
O
O
O
R
1
O
R
O
H
O
O
O
O
O
O
R 1
O
R
O
HO
O
HO
O
R
1
COOH
46
– CO
HO
R
O
CO
Scheme 5 Rearrangement of 11-O-acyl-slovanolide to give 8-acetyl-1,5-dimethylazulene (46)