Synthesis of Mesembrine

C17H23NO3
Principal investigator | Maurice Shamma |
---|---|
Publication year | 1965 |
Synthesis type | Total |
Number of steps | 20 (linear) |
References |
Part 1 of 1



H2,
Pd/C
3 atm
EtOH
70% (2 steps)

NaH,
AllylBr
PhH
Reflux, 10 h, 95%

LiAlH4
Et2O
RT, 2 h, 70%

Ac2O
Pyr
Reflux, 2 h, 92%



(COCl)2
PhH
RT, 2 h

MeNH2
PhH
0 °C, 93% (2 steps)

LiAlH4
Dioxane , THF
Reflux, 17 h, 90%

HCO2Et
Et3N
Reflux, ON, 92%


PhNMe3+ Br3-
THF
RT, 19 h

CaCO3
DMF
Reflux, 2 h, 79% (2 steps)


NaOAc,
Cr(OAc)2
Acetone, AcOH
40%

NaBH4
EtOH
RT, ON, 95%

O2,
Pt
EtOAc
RT, 3 d

