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