Synthesis of Mersicarpine

Structure of Mersicarpine

C17H20N2O2

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