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Named reactions

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Reserpine

Chemical structure of Reserpine
C33H40N2O9
Author Robert B. Woodward
Publication year 1956
Synthesis type Total synthesis
Number of steps 28 (3 parts)
References

Browse hundreds of other total syntheses.

Part 1 of 3
Chemical structure
  1. NaNO2, HCl
  2. (CH2O)n, NH2OH.HCl, NaOAc, CuSO4
H2O
0-5 °C
Chemical structure
NH4FeSO4.12H2O
H2O
40 min, 63% (2 steps)
Chemical structure
MeNO2, NH4OAc
AcOH
Reflux, 2 h, 65%

See the Henry Reaction
Chemical structure
H2, Pd/C
3.4 atm
EtOAc, EtOH, AcOH
RT, 55%

See the Leimgruber-Batcho Indole Synthesis
Chemical structure
(COCl)2
Et2O
0 °C, 30 min, 90%
Chemical structure
NH3
H2O
40-50 °C, 30 min, 90%
Chemical structure
LiAlH4
THF
Reflux, ON, 63%
Chemical structure

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Part 2 of 3
Chemical structure
+
Chemical structure
PhH
Reflux, 10 h, 8%

See the Diels-Alder Reaction
"[This method was not] investigated extensively with a view to determining optimum conditions."
Chemical structure
Al(Oi-Pr)3
i-PrOH
Reflux, 60 min, 60%

See the Meerwein-Ponndorf-Verley Reduction
Chemical structure
Br2
MeOH
RT, 45 min, 46%
Chemical structure
NaOMe
MeOH
RT, 2.5 h, 84%
Chemical structure
NBS, H2SO4
H2O
60 to 90 °C, 40 min
Chemical structure
CrO3
AcOH, H2O
RT, 10 h, 60% (2 steps)

See the Jones Oxidation
Chemical structure
Zn
AcOH
17 °C, 2 min, 79%
Chemical structure
CH2N2
Dioxane , Et2O
10 °C, 96%
Chemical structure
Ac2O
Pyr
80-90 °C, 2 h, 92%
Chemical structure
OsO4, KClO3
H2O, CCl4
RT, 8 h, 46%
Chemical structure
HIO4
H2O
RT, 20 min
Chemical structure
CH2N2
Et2O
0 °C, 3 min
Chemical structure

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Part 3 of 3
Chemical structure
+
Chemical structure
PhH
RT, 3 min
Chemical structure
NaBH4
MeOH
RT to Reflux, 10 min, 81% (4 steps)
Chemical structure
POCl3
Reflux, 2 h

See the Bischler-Napieralski Reaction
Chemical structure
NaBH4
MeOH, H2O
RT, 5 min, 70%
Chemical structure
KOH
MeOH, H2O
Reflux, 2 h, 100%
Chemical structure
DCC
Pyr
100 °C, 2 h, 67%

See the Steglich Esterification
Chemical structure
t-BuCO2H
Xylene(s)
Reflux, 16 h, 74%
Chemical structure
NaOMe
MeOH
Reflux, 90 min, 79%
Chemical structure + Chemical structure
Pyr
RT, 4 d, 57%
Chemical structure

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