Synthesis of Reserpine

Structure of Reserpine

C33H40N2O9

Principal investigatorStephen Hanessian
Publication year1997
Synthesis typeTotal
Number of steps 22 (linear)
References
J. Org. Chem. 1997, 62, 465.
Part 1 of 1
intermediate structure
BnBr, TsOH, n-Bu2SnO
Dean-Stark
DMF, PhH
Reflux, 22 h, 81%
intermediate structure
KH, MeI
THF
RT to Reflux, 2 h, 90%
See the Williamson Ether Synthesis
intermediate structure
H2, Pd(OH)2/C
1 atm
MeOH
RT, 98%
intermediate structure
NaIO4, RuO2
Acetone, EtOAc, H2O
RT, 16 h, 90%
intermediate structure
KHCO3
MeOH
RT, 12 h, 90%
intermediate structure
2,6-Lutidine, TBSOTf
CH2Cl2
0 °C, 15 min, 90%
intermediate structure
VinylMgBr
THF
-78 °C, 2 h, 90%
See the Grignard Reaction
intermediate structure + intermediate structure
DCC, DMAP
CH2Cl2
RT, 40 h, 86%
See the Steglich Esterification
intermediate structure
NaI
3 Å MS
MeCN
RT, 18 h, 97%
See the Finkelstein Reaction
intermediate structure
Ph3SnH, AIBN
PhH
Reflux, 5.5 h, 51%
"Also isolated was the C4-epimer (22 % yield) which can be equilibrated to the desired product."
intermediate structure
  1. O3
  2. Me2S
CH2Cl2
-78 °C to RT
intermediate structure
NaH2PO4, NaClO2, 2-Methyl-2-butene
H2O, t-BuOH
RT, 2 h
See the Pinnick-Lindgren Oxidation
intermediate structure
CH2N2
Et2O
0 °C, 5 min, 91% (3 steps)
intermediate structure
Sia2BH
THF
0 °C to RT, 4 h, 98%
intermediate structure + intermediate structure
t-BuCO2H
PhMe
Reflux, 50 min, 53%
See the Pictet-Spengler Reaction
"Also isolated was the C3-epimer (37 % yield)."
intermediate structure
2,6-Lutidine, TMSOTf
CH2Cl2
RT, 4 h, 100%
intermediate structure
BH3.THF
THF
RT, 6 h, 84%
intermediate structure
HF
H2O, MeCN
0 °C to RT, 30 min
intermediate structure
2,6-Lutidine, TBSOTf
CH2Cl2
0 °C, 10 min
intermediate structure
SmI2, HMPA
Ethylene Glycol, THF
RT, 8 h, 30% (3 steps)
intermediate structure
HF
H2O, MeCN
RT, 3 h
intermediate structure + intermediate structure
DMAP, Et3N
CH2Cl2
RT, ON, 80% (2 steps)
intermediate structure
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