Synthesis of Strychnine

Structure of Strychnine

C21H22N2O2

Principal investigatorJoan Bosch
Publication year2000
Synthesis typeTotal
Number of steps 14 (linear)
References
Part 1 of 1
intermediate structure
O3
CH2Cl2
-78 °C, 3 h
intermediate structure + intermediate structure
NaBH3CN
i-PrOH
RT, 2 d, 37% (2 steps)
intermediate structure
ClCO2CH(Cl)CH3
135 °C, 2 d, 72%
intermediate structure
TMSI, TMS2NH
CH2Cl2, Pentane
-20 °C, 6 h, 100%
intermediate structure
PhSeCl, (PhSe)2
THF
-35 °C to RT, 4.5 h, 70%
intermediate structure
O3, i-Pr2NH
CH2Cl2
-78 °C to RT, , 72%
intermediate structure
MeOH
Reflux, 3 h, 100%
intermediate structure + intermediate structure
K2CO3, LiI
MeCN
50 °C, 3 h, 74%
intermediate structure
Pd(OAc)2, Ph3P
Et3N
90 °C, 90 min, 53%
See the Heck Coupling
intermediate structure
MeO2CCN, TMS2NLi
THF, HMPA
-78 °C to RT, 4.5 h, 62%
"The yield was 67 % brsm."
intermediate structure
Zn, H2SO4
MeOH
Reflux, 2 h, 36%
intermediate structure
NaOMe
MeOH
Reflux, 5 h, 72%
intermediate structure
i-Bu2AlH
PhMe
-40 °C, 25 min
intermediate structure
Malonic Acid, NaOAc
AcOH, Ac2O
110 °C, 2 h, 49% (2 steps)
See the Aldol Addition
intermediate structure