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Named reactions

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Search synthesis

Reserpine

Chemical structure of Reserpine
C33H40N2O9
Author Stephen Hanessian
Publication year 1997
Synthesis type Total synthesis
Number of steps 22 (linear)
Reference

Browse hundreds of other total syntheses.

Part 1 of 1
Chemical structure
TsOH, n-Bu2SnO, BnBr
Dean-Stark
PhH, DMF
Reflux, 22 h, 81%
Chemical structure
KH, MeI
THF
RT to Reflux, 2 h, 90%

See the Williamson Ether Synthesis
Chemical structure
H2, Pd(OH)2/C
1 atm
MeOH
RT, 98%
Chemical structure
RuO2, NaIO4
EtOAc, Acetone, H2O
RT, 16 h, 90%
Chemical structure
KHCO3
MeOH
RT, 12 h, 90%
Chemical structure
TBSOTf, 2,6-Lutidine
CH2Cl2
0 °C, 15 min, 90%
Chemical structure
VinylMgBr
THF
-78 °C, 2 h, 90%

See the Grignard Reaction
Chemical structure + Chemical structure
DCC, DMAP
CH2Cl2
RT, 40 h, 86%

See the Steglich Esterification
Chemical structure
NaI
3 Å MS
MeCN
RT, 18 h, 97%

See the Finkelstein Reaction
Chemical 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.
Chemical structure
  1. O3
  2. Me2S
CH2Cl2
-78 °C to RT
Chemical structure
NaClO2, 2-Methyl-2-butene, NaH2PO4
t-BuOH, H2O
RT, 2 h

See the Pinnick-Lindgren Oxidation
Chemical structure
CH2N2
Et2O
0 °C, 5 min, 91% (3 steps)
Chemical structure
Sia2BH
THF
0 °C to RT, 4 h, 98%
Chemical structure + Chemical structure
t-BuCO2H
PhMe
Reflux, 50 min, 53%

See the Pictet-Spengler Reaction
Also isolated was the C3-epimer (37 % yield).
Chemical structure
TMSOTf, 2,6-Lutidine
CH2Cl2
RT, 4 h, 100%
Chemical structure
BH3.THF
THF
RT, 6 h, 84%
Chemical structure
HF
MeCN, H2O
0 °C to RT, 30 min
Chemical structure
TBSOTf, 2,6-Lutidine
CH2Cl2
0 °C, 10 min
Chemical structure
SmI2, HMPA
Ethylene Glycol, THF
RT, 8 h, 30% (3 steps)
Chemical structure
HF
MeCN, H2O
RT, 3 h
Chemical structure + Chemical structure
Et3N, DMAP
CH2Cl2
RT, ON, 80% (2 steps)
Chemical structure

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