Synthesis of Reserpine

Structure of Reserpine

C33H40N2O9

Principal investigatorGilbert Stork
Publication year2005
Synthesis typeTotal
Number of steps 12 (linear)
References
Part 1 of 1
intermediate structure
  1. n-BuLi
  2. Me2SiHCl
Et2O
-25 °C to Reflux, 8 h, 85%
intermediate structure + intermediate structure
Co2(CO)8
PhH
45-47 °C, 2 h, 33%
intermediate structure + intermediate structure
i-Pr2NLi
THF
-78 to 0 °C, 3 h, 88%
intermediate structure
n-Bu4N+ F-
THF
RT, 2 min, 84%
intermediate structure
H2, Pd/C
EtOAc
RT, 30 h, 98%
intermediate structure
DMAP, Pyr, TsCl
CH2Cl2
55 °C, 10 h, 72%
intermediate structure
mCPBA, Na2HPO4
CH2Cl2
RT, 15 h, 61%
intermediate structure
MeI, Ag2O, CaSO4
RT, 20 h, 96%
intermediate structure
i-Bu2AlH
Et2O, THF
-78 °C, 30 min, 84%
intermediate structure + intermediate structure
KCN, MgSO4
MeCN
RT, 70 min, 87%
intermediate structure
HCl
H2O, THF
RT, 30 h, 92%
intermediate structure + intermediate structure
Pyr
RT, 4 d, 95%
intermediate structure