Synthesis of Mersicarpine

Structure of Mersicarpine

C17H20N2O2

Principal investigatorMichael A. Kerr
Publication year2008
Synthesis typeTotal
Number of steps 14 (linear)
References
Org. Lett. 2008, 10, 1437.
Part 1 of 1
intermediate structure + intermediate structure
K2CO3
THF
0 °C, 20 min, 97%
intermediate structure
DDQ
PhMe
Reflux, 12 h, 81%
intermediate structure + intermediate structure
K2CO3
THF
Reflux, 4 h, 98%
See the Michael Addition
intermediate structure
Mn(OAc)3.2H2O
AcOH
Reflux, 3 h, 60%
intermediate structure
NaHCO3
MeOH
RT, 6 h, 95%
intermediate structure
KOt-Bu, VinylCN
THF
0 °C, 20 min, 74%
See the Michael Addition
intermediate structure
NaBH4
THF
RT, 16 h, 100%
intermediate structure
  1. NaH
  2. CS2
  3. MeI
THF
0 °C, 2.5 h, 73%
intermediate structure
DME
170 °C, 5 h, 74%
See the Chugaev Elimination
"Overall yield after the recovered starting material was resubmitted to the same conditions."
intermediate structure
PtO2, H2
1 atm
CHCl3, EtOH
RT, 16 h
intermediate structure
Boc2O, Et3N
CH2Cl2
RT, 30 min, 71% (2 steps)
intermediate structure
NaHCO3, Oxone, n-Bu4N+ HSO4-, Na2EDTA
Acetone, H2O, MeCN
0 °C, 2.5 h, 93%
intermediate structure
2,6-Lutidine, TBSOTf
CH2Cl2
0 °C to RT, ON
intermediate structure
n-Bu4N+ F-
THF
RT, 60 min, 82% (2 steps)
intermediate structure
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