Synthesis of Oscillarin
C34H44N6O5
| Principal investigator | Stephen Hanessian |
|---|---|
| Publication year | 2004 |
| Synthesis type | Total |
| Number of steps | 17 (2 parts) |
| References |
Part 1 of 2
+
+
HOBt,
EDC
CH2Cl2, Et3N
RT, ON, 89%
H2,
Pd/C
1 atm
EtOAc, MeOH
RT, ON, 100%
Part 2 of 2
+
+
+
TMS2NLi
THF
-78 °C, 20 min, 85%
HCO2H
RT, 5 h
PhMe
Reflux, 90 min
Boc2O,
DMAP
CH2Cl2, Et3N
RT, ON, 83% (3 steps)
LiBHEt3
THF
-78 °C, 60 min
DMAP,
Ac2O
CH2Cl2, Et3N
RT, ON, 91% (2 steps)
n-Bu4N+ OAc-
PhMe
40-50 °C, 2 h, 78%
CF3CO2H
CH2Cl2
RT, 30 min
EDC,
HOBt
CH2Cl2, Et3N
0 °C to RT, ON, 91% (2 steps)
NaOMe
MeOH
RT, 4 h
MeOCH2Cl,
i-Pr2NEt
CH2Cl2
RT, ON, 80% (2 steps)
LiOH
H2O, THF
RT, 7 h
+
EDC,
HOBt
CH2Cl2, Et3N
0 °C to RT, ON, 86% (2 steps)
"For the synthesis of this amine, see the synthesis of Dysinosin A by Stephen Hanessian (2002)."
HCl
H2O, THF
RT, 4 h, 70%