From Plant to Patient: Thapsigargin, a Tool for Understanding …
73
O
O
O
O
O
O
O
O
O
OH
OH
O
a
O
O
O
O
O
O
OH
O
O
OH
OH
O
b
O
O
O
O
O
O
S
O
O
OH
OH
O
c
O
O
O
O
O
O
O
O
OH
OH
O
1
54
55
56
Scheme 10 a lithium borohydride in diethyl ether; b CH 3 CH 2 SH added HCl; c (C 6 H 5 ) 3 SnH
2,2´–azo-isobutyronitrile
O
O
O
O
O
O
OH
O
O
OH
OH
O
54
a
O
O
O
O
O
O
O
O
OH
O
57
O
O
O
O
O
O
O
O
O
O
O
O
OH
OH
O
58
+
b
O
O
O
O
O
O
O
O
O
OH
OH
O
59
O
Scheme 11 Chemistry of the lactols 54. a triethyl orthoformate p-toluenesulfonic acid; b triethyl
orthoacetate