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Named reactions

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Search synthesis

Mersicarpine

Chemical structure of Mersicarpine
C17H20N2O2
Author Michael A. Kerr
Publication year 2008
Synthesis type Total synthesis
Number of steps 14 (linear)
Reference

Browse hundreds of other total syntheses.

Part 1 of 1
Chemical structure
+
Chemical structure
K2CO3
THF
0 °C, 20 min, 97%
Chemical structure
DDQ
PhMe
Reflux, 12 h, 81%
Chemical structure + Chemical structure
K2CO3
THF
Reflux, 4 h, 98%

See the Michael Addition
Chemical structure
Mn(OAc)3.2H2O
AcOH
Reflux, 3 h, 60%
Chemical structure
NaHCO3
MeOH
RT, 6 h, 95%
Chemical structure
VinylCN, KOt-Bu
THF
0 °C, 20 min, 74%

See the Michael Addition
Chemical structure
NaBH4
THF
RT, 16 h, 100%
Chemical structure
  1. NaH
  2. CS2
  3. MeI
THF
0 °C, 2.5 h, 73%
Chemical structure
DME
170 °C, 5 h, 74%

See the Chugaev Elimination
Overall yield after the recovered starting material was resubmitted to the same conditions.
Chemical structure
H2, PtO2
1 atm
EtOH, CHCl3
RT, 16 h
Chemical structure
Boc2O, Et3N
CH2Cl2
RT, 30 min, 71% (2 steps)
Chemical structure
Oxone ®, n-Bu4N+ HSO4-, NaHCO3, Na2EDTA
MeCN, Acetone, H2O
0 °C, 2.5 h, 93%
Chemical structure
TBSOTf, 2,6-Lutidine
CH2Cl2
0 °C to RT, ON
Chemical structure
n-Bu4N+ F-
THF
RT, 60 min, 82% (2 steps)
Chemical structure

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