Synthesis of Physostigmine

Structure of Physostigmine

C15H21N3O2

Principal investigatorPercy L. Julian
Publication year1935
Synthesis typeTotal
Number of steps 10 (linear)
References
J. Am. Chem. Soc. 1935, 57, 755. J. Am. Chem. Soc. 1935, 57, 563. Bull. Soc. Chim. Fr. 1916, 19, 33.
Part 1 of 1
intermediate structure
  1. Na
  2. Me2SO4
  3. EtOH , KOH , H2O
Xylene(s)
Reflux, 38 h, 96%
intermediate structure
Special reagent
PhH
Reflux, 30 min
intermediate structure
AlCl3
RT to 185 °C, 92% (2 steps)
See the Stollé Synthesis
intermediate structure
Et2SO4, KOH
H2O
100 °C, 30 min, 68%
See the Williamson Ether Synthesis
intermediate structure
ClCH2CN, NaOEt
EtOH
60 °C, 3 h, 84%
intermediate structure
H2SO4, PtO2, H2
1.5 atm
AcOH
RT, 91%
intermediate structure
  1. PhCHO
  2. MeI
  3. HCl , H2O , EtOH
RT to 100 °C, 3 h, 91%
See the Forster-Decker Amine Synthesis
intermediate structure
Na
EtOH
RT, 2 h, 80%
intermediate structure
AlCl3
Petroleum ether
Reflux, ON, 91%
intermediate structure
  1. Na
  2. MeNCO
Et2O, PhH
RT, 60 min, 50%
intermediate structure
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