Synthesis of Mesembrine

Structure of Mesembrine

C17H23NO3

Principal investigatorMaurice Shamma
Publication year1965
Synthesis typeTotal
Number of steps 20 (linear)
References
Tetrahedron Lett. 1965, 6, 4847.
Part 1 of 1
intermediate structure
1,3-Butadiene
PhMe
See the Diels-Alder Reaction
"No yield given."
intermediate structure
HCl, NaOEt
EtOH, H2O
0 °C to RT, 2.5 h
See the Nef Reaction
intermediate structure
H2, Pd/C
3 atm
EtOH
70% (2 steps)
intermediate structure
NaH, AllylBr
PhH
Reflux, 10 h, 95%
intermediate structure
LiAlH4
Et2O
RT, 2 h, 70%
intermediate structure
Ac2O
Pyr
Reflux, 2 h, 92%
intermediate structure
OsO4, NaIO4
Dioxane , H2O
RT, ON, 79%
See the Lemieux-Johnson Oxidation
intermediate structure
AgNO3, KOH
EtOH, H2O
RT, 2 h, 93%
See the Tollens Oxidation
intermediate structure
(COCl)2
PhH
RT, 2 h
intermediate structure
MeNH2
PhH
0 °C, 93% (2 steps)
intermediate structure
LiAlH4
Dioxane , THF
Reflux, 17 h, 90%
intermediate structure
HCO2Et
Et3N
Reflux, ON, 92%
intermediate structure
H2SO4, Na2Cr2O7
Acetone, H2O
80%
See the Jones Oxidation
intermediate structure
PhNMe3+ Br3-
THF
RT, 19 h
intermediate structure
CaCO3
DMF
Reflux, 2 h, 79% (2 steps)
intermediate structure
NaOCl
H2O, Pyr
0 °C, 60 min, 90%
See the Michael Addition
intermediate structure
NaOAc, Cr(OAc)2
Acetone, AcOH
40%
intermediate structure
NaBH4
EtOH
RT, ON, 95%
intermediate structure
O2, Pt
EtOAc
RT, 3 d
intermediate structure
HCl
EtOH, H2O
Reflux, 4 h, 50% (2 steps)
See the Michael Addition
intermediate structure
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