Synthesis of Mersicarpine

C17H20N2O2
Principal investigator | Tohru Fukuyama |
---|---|
Publication year | 2010 |
Synthesis type | Total |
Number of steps | 14 (linear) |
References |
Part 1 of 1

Pyrrolidine
Dean-Stark
PhH
Reflux, ON



TsOH
Dean-Stark
PhMe
Reflux, ON

- Hydroquinone , Methyl acrylate
- 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."

IBX
DMSO
85 °C, 72%

NaOH,
H2O2
H2O, MeOH
0 °C, 1 h, 88%


NaOAc.3H2O
EtOH, H2O
RT, 7 h, 89%


NaBH4
MeOH
0 °C, 15 min, 87%


NaAuCl4.2H2O
EtOH
RT, 48 h, 78%

HCl,
NaNO2,
NaOAc,
PhNH2
Dioxane , H2O, i-PrOH
0 °C, 2 h, 97%

- NaH
- Et3N , MsCl
4 A MS
PhMe
0 °C to RT, 15 min, 77%

- H2 , Pd/C
- NaHCO3
- O2
- Me2S
CH2Cl2, i-PrOH
RT to Reflux, 23.5 h, 96%
