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Named reactions

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Oscillarin

"This paper is dedicated to Professors Nico Speckamp, Larry Overman, and David Hart for their seminal contributions to N-acyliminium chemistry."

Chemical structure of Oscillarin
C34H44N6O5
Author Stephen Hanessian
Publication year 2004
Synthesis type Total synthesis
Number of steps 17 (2 parts)
References

Browse hundreds of other total syntheses.

Part 1 of 2
Chemical structure
+
Chemical structure
EDC, HOBt
CH2Cl2, Et3N
RT, ON, 89%
Chemical structure
H2, Pd/C
1 atm
MeOH, EtOAc
RT, ON, 100%
Chemical structure

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Part 2 of 2
Chemical structure
+
Chemical structure
TMS2NLi
THF
-78 °C, 20 min, 85%
Chemical structure
HCO2H
RT, 5 h
Chemical structure
PhMe
Reflux, 90 min
Chemical structure
Boc2O, DMAP
CH2Cl2, Et3N
RT, ON, 83% (3 steps)
Chemical structure
LiBHEt3
THF
-78 °C, 60 min
Chemical structure
Ac2O, DMAP
CH2Cl2, Et3N
RT, ON, 91% (2 steps)
Chemical structure
SnBr4
CH2Cl2
-78 °C, 10 min, 78%

See the Prins Reaction
Chemical structure
n-Bu4N+ OAc-
PhMe
40-50 °C, 2 h, 78%
Chemical structure
CF3CO2H
CH2Cl2
RT, 30 min
Chemical structure
EDC, HOBt
CH2Cl2, Et3N
0 °C to RT, ON, 91% (2 steps)
Chemical structure
NaOMe
MeOH
RT, 4 h
Chemical structure
MeOCH2Cl, i-Pr2NEt
CH2Cl2
RT, ON, 80% (2 steps)
Chemical structure
LiOH
THF, H2O
RT, 7 h
Chemical structure + Chemical 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).
Chemical structure
HCl
THF, H2O
RT, 4 h, 70%
Chemical structure

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