Synthesis of Mersicarpine

Structure of Mersicarpine

C17H20N2O2

Principal investigatorTohru Fukuyama
Publication year2010
Synthesis typeTotal
Number of steps 14 (linear)
References
J. Am. Chem. Soc. 2010, 132, 1236.
Part 1 of 1
intermediate structure
Pyrrolidine
Dean-Stark
PhH
Reflux, ON
intermediate structure
  1. EtI
  2. H2O
EtOH
Reflux, ON, 32% (2 steps)
See the Stork Enamine Synthesis
intermediate structure
Special reagent
TsOH
Dean-Stark
PhMe
Reflux, ON
intermediate structure
  1. Hydroquinone , Methyl acrylate
  2. H2O , THF , AcOH
RT to 65 °C, 2 d, 78% (2 steps)
See the Michael Addition
"94:06 e.r.; the enantiomeric purity was improved to >99:01 e.r. by crystallization of the corresponding semicarbazone."
intermediate structure
IBX
DMSO
85 °C, 72%
intermediate structure
NaOH, H2O2
H2O, MeOH
0 °C, 1 h, 88%
intermediate structure
Special reagent
NaOAc.3H2O
EtOH, H2O
RT, 7 h, 89%
intermediate structure
Pb(OAc)4
CH2Cl2
-10 °C, 1 h, 60%
See the Eschenmoser Fragmentation
intermediate structure
NaBH4
MeOH
0 °C, 15 min, 87%
intermediate structure
Special reagent
CuI, Et3N, Pd(PPh3)4
DMF
80 °C, 2 d, 78%
See the Sonogashira Coupling
intermediate structure
NaAuCl4.2H2O
EtOH
RT, 48 h, 78%
intermediate structure
HCl, NaNO2, NaOAc, PhNH2
Dioxane , H2O, i-PrOH
0 °C, 2 h, 97%
intermediate structure
  1. NaH
  2. Et3N , MsCl
4 A MS
PhMe
0 °C to RT, 15 min, 77%
intermediate structure
  1. H2 , Pd/C
  2. NaHCO3
  3. O2
  4. Me2S
CH2Cl2, i-PrOH
RT to Reflux, 23.5 h, 96%
intermediate structure
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