Synthesis of Reserpine

C33H40N2O9
Principal investigator | Gilbert Stork |
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Publication year | 2005 |
Synthesis type | Total |
Number of steps | 12 (linear) |
References |
Part 1 of 1
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- n-BuLi
- Me2SiHCl
Et2O
-25 °C to Reflux, 8 h, 85%


Co2(CO)8
PhH
45-47 °C, 2 h, 33%



n-Bu4N+ F-
THF
RT, 2 min, 84%

Pd/C,
H2
1 atm
EtOAc
RT, 30 h, 98%

TsCl,
Pyr,
DMAP
CH2Cl2
55 °C, 10 h, 72%

Na2HPO4,
mCPBA
CH2Cl2
RT, 15 h, 61%
See the Baeyer-Villiger Oxidation
See the Fleming-Tamao Oxidation

CaSO4,
Ag2O,
MeI
RT, 20 h, 96%

i-Bu2AlH
Et2O, THF
-78 °C, 30 min, 84%


MgSO4,
KCN
MeCN
RT, 70 min, 87%



Pyr
RT, 4 d, 95%
