Synthesis of Reserpine

C33H40N2O9
Principal investigator | Robert B. Woodward |
---|---|
Publication year | 1956 |
Synthesis type | Total |
Number of steps | 28 (3 parts) |
References |
Part 1 of 3

- NaNO2 , HCl
- CuSO4 , NH2OH.HCl , NaOAc , (CH2O)n
H2O
0-5 °C

NH4FeSO4.12H2O
H2O
40 min, 63% (2 steps)



(COCl)2
Et2O
0 °C, 30 min, 90%

NH3
H2O
40-50 °C, 30 min, 90%

LiAlH4
THF
Reflux, ON, 63%

Part 2 of 3
+


PhH
Reflux, 10 h, 8%
See the Diels-Alder Reaction
""[This method was not] investigated extensively with a view to determining optimum conditions.""


Br2
MeOH
RT, 45 min, 46%

NaOMe
MeOH
RT, 2.5 h, 84%

NBS,
H2SO4
H2O
60 to 90 °C, 40 min


Zn
AcOH
17 °C, 2 min, 79%

CH2N2
Dioxane , Et2O
10 °C, 96%

Ac2O
Pyr
80-90 °C, 2 h, 92%

OsO4,
KClO3
CCl4, H2O
RT, 8 h, 46%

HIO4
H2O
RT, 20 min

CH2N2
Et2O
0 °C, 3 min

Part 3 of 3
+
+


PhH
RT, 3 min

NaBH4
MeOH
RT to Reflux, 10 min, 81% (4 steps)


NaBH4
H2O, MeOH
RT, 5 min, 70%

KOH
H2O, MeOH
Reflux, 2 h, 100%


t-BuCO2H
Xylene(s)
Reflux, 16 h, 74%

NaOMe
MeOH
Reflux, 90 min, 79%


Pyr
RT, 4 d, 57%
