Sample reactions
intermediate structure
SnBr4
CH2Cl2
-78 °C, 10 min, 78%
intermediate structure
intermediate structure
SnBr4
CH2Cl2
-78 °C, 5 min, 60%
intermediate structure
intermediate structure
Me2NH, ZnBr2
MeCN
50 °C, 40 min, 65% (3 steps)
intermediate structure
intermediate structure
NBS
DMSO, H2O
10 °C, 2 h, 32%
"Also isolated was the C2-epimer which was reverted to the starting material with zinc/ammonium chloride (52 % yield)."
intermediate structure
intermediate structure
CH2Cl2
-23 to 0 °C, 2.5 h
intermediate structure
intermediate structure intermediate structure
TsOH
CH2Cl2
-30 °C to RT, 17 h, 65%
intermediate structure
intermediate structure intermediate structure
TsOH
CH2Cl2
-50 °C to RT, 17.5 h, 65%
intermediate structure
intermediate structure
CH2O
Buffer (pH = 7)
RT, 60 min, 50% (2 steps)
intermediate structure
intermediate structure
SnCl4
CH2Cl2
0 °C to RT, 14.5 h, 32%
intermediate structure