Synthesis of Oscillarin

Structure of Oscillarin

C34H44N6O5

Principal investigatorStephen Hanessian
Publication year2004
Synthesis typeTotal
Number of steps 17 (2 parts)
References
Part 1 of 2
intermediate structure + intermediate structure
EDC, HOBt
CH2Cl2, Et3N
RT, ON, 89%
intermediate structure
H2, Pd/C
MeOH, EtOAc
RT, ON, 100%
intermediate structure
Part 2 of 2
intermediate structure + intermediate structure
TMS2NLi
THF
-78 °C, 20 min, 85%
intermediate structure
HCO2H
RT, 5 h
intermediate structure
PhMe
Reflux, 90 min
intermediate structure
Boc2O, DMAP
CH2Cl2, Et3N
RT, ON, 83% (3 steps)
intermediate structure
LiBHEt3
THF
-78 °C, 60 min
intermediate structure
Ac2O, DMAP
CH2Cl2, Et3N
RT, ON, 91% (2 steps)
intermediate structure
SnBr4
CH2Cl2
-78 °C, 10 min, 78%
See the Prins Reaction
intermediate structure
n-Bu4N+ OAc-
PhMe
40-50 °C, 2 h, 78%
intermediate structure
CF3CO2H
CH2Cl2
RT, 30 min
intermediate structure
EDC, HOBt
CH2Cl2, Et3N
0 °C to RT, ON, 91% (2 steps)
intermediate structure
NaOMe
MeOH
RT, 4 h
intermediate structure
MeOCH2Cl, i-Pr2NEt
CH2Cl2
RT, ON, 80% (2 steps)
intermediate structure
LiOH
THF, H2O
RT, 7 h
intermediate structure + intermediate structure
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)."
intermediate structure
HCl
THF, H2O
RT, 4 h, 70%
intermediate structure