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
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HOBt,
EDC
CH2Cl2, Et3N
RT, ON, 89%

H2,
Pd/C
1 atm
EtOAc, MeOH
RT, ON, 100%

Part 2 of 2
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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%
