Synthesis of Strychnofoline

C30H34N4O2
Principal investigator | Erick M. Carreira |
---|---|
Publication year | 2002 |
Synthesis type | Total |
Number of steps | 22 (3 parts) |
References |
Part 1 of 3

BnBr,
NaH
DMF
-78 °C to RT, 65 min, 72%


BBr3
CH2Cl2
-78 to 0 °C, 5 h, 92%

TBSCl,
Imidazole
DMF
RT, 3 h, 88%

Br(CH2)2Br,
NaH
DMF
0 °C, 1 h, 86%

BnBr,
NaH
DMF
-45 to 0 °C, 95 min, 87%

Part 2 of 3

TMS2NLi,
PhSeCl
THF
-78, 2 h

H2O2
EtOAc, H2O
0 °C to RT, 1h, 80%


i-Bu2AlH
THF
-78 °C, 2 h

HCl
CH2Cl2, H2O
RT, 5 min, 90% (2 steps)

Et3N,
TMSOTf
CH2Cl2
-78 to -20 °C, 2 h, 100%

Part 3 of 3
+
+


MgI2
Sealed Tube
THF
80 °C, 16 h, 55%

OsO4
Dioxane , H2O, t-BuOH
RT, 4 h

NaIO4
Dioxane , H2O, t-BuOH
RT, 2 h, 86% (2 steps)

TsOH,
HC(OMe)3
MeOH
RT, ON, 93 %

n-Bu4N+ F-
THF
0 °C, 5 h, 86%

IBX
DMSO
RT, 12 h, 88%


HCl
Acetone, H2O
RT, 12 h, 94%



