Synthesis of Mersicarpine

C17H20N2O2
Principal investigator | Michael A. Kerr |
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Publication year | 2008 |
Synthesis type | Total |
Number of steps | 14 (linear) |
References |
Part 1 of 1
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K2CO3
THF
0 °C, 20 min, 97%

DDQ
PhMe
Reflux, 12 h, 81%



Mn(OAc)3.2H2O
AcOH
Reflux, 3 h, 60%

NaHCO3
MeOH
RT, 6 h, 95%


NaBH4
THF
RT, 16 h, 100%

- NaH
- CS2
- MeI
THF
0 °C, 2.5 h, 73%

DME
170 °C, 5 h, 74%
See the Chugaev Elimination
"Overall yield after the recovered starting material was resubmitted to the same conditions."

PtO2,
H2
1 atm
CHCl3, EtOH
RT, 16 h

Boc2O,
Et3N
CH2Cl2
RT, 30 min, 71% (2 steps)

NaHCO3,
Oxone,
n-Bu4N+ HSO4-,
Na2EDTA
Acetone, H2O, MeCN
0 °C, 2.5 h, 93%

2,6-Lutidine,
TBSOTf
CH2Cl2
0 °C to RT, ON

n-Bu4N+ F-
THF
RT, 60 min, 82% (2 steps)
