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Named reactions

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Cholesterol

Chemical structure of Cholesterol
C27H46O
Author Robert B. Woodward
Publication year 1951
Synthesis type Formal synthesis
Number of steps 39 (linear)
References

Browse hundreds of other total syntheses.

Part 1 of 1
Chemical structure
1,3-Butadiene
PhH
100 °C, 96 h, 86 %

See the Diels-Alder Reaction
Chemical structure
NaOH
Dioxane , H2O
40-50 °C, 90 %
Chemical structure
LiAlH4
THF
Reflux, 65 min, 64 %
Chemical structure
H2SO4
Dioxane , H2O
RT, 24 h, 99 %
Chemical structure
Ac2O
Pyr
RT, 12 h, 96 %
Chemical structure
Zn
Ac2O
Reflux, 8 min, 63 %
Chemical structure
HCO2Et, NaOMe
PhH
RT, 30 min, 94 %

See the Claisen Condensation
Chemical structure
Ethyl vinyl ketone, KOt-Bu, NaOH
t-BuOH, H2O
0 °C to RT, 10 h, 53 %

See the Michael Addition
Chemical structure
KOH
Dioxane , H2O
0 °C, 3 h, 88 %
Chemical structure
OsO4
Et2O
0 °C, 5-8 d, 57 %

A single, uncharacterized isomer was isolated.
Chemical structure
CuSO4
Acetone
RT, 36 h, 83 %
Chemical structure
H2, Pd/SrCO3
1 atm
PhH
RT, 3.5 h, 85 %
Chemical structure
HCO2Et, NaOMe
PhH
RT, ON

See the Claisen Condensation
Chemical structure
PhNHMe
MeOH
RT, 24 h, 88 % (2 steps)
Chemical structure
VinylCN, Me3N+Bn HO-
PhH, t-BuOH, H2O
50 °C, 45 h

See the Michael Addition
Chemical structure
KOH
H2O
Reflux, 46 % (2 steps)

Also isolated was the C1-epimer (33 % yield).
Chemical structure
NaOAc
Ac2O
Reflux, 2 h, 28 %
Chemical structure
MeMgBr
PhH, Et2O
-18 °C, 3 h

See the Grignard Reaction
Chemical structure
NaOH
MeOH, H2O
Reflux, 2 h, 58 % (2 steps)

See the Aldol Condensation
Chemical structure
HIO4
Dioxane , H2O
0 °C, 14 h
Chemical structure
Piperidine, AcOH
Dean-Stark
PhH
60 °C, 60 min, 66 % (2 steps)

See the Aldol Condensation
Chemical structure
Na2Cr2O7
AcOH, H2O
RT, 10 h
Chemical structure
CH2N2
PhH, Et2O
RT, 20 min, 30 % (2 steps)
Chemical structure
H2, PtO2
1 atm
AcOH
RT
Chemical structure
CrO3
AcOH
RT, ON, 2.4 % (2 steps)
Chemical structure
NaBH4
EtOH
RT, 4 h, 64 %
Chemical structure
KOH
MeOH, H2O
Reflux, 12 h, 100 %
Chemical structure
Ac2O
Pyr
60 °C, 3 h, 92 %
Chemical structure
SOCl2
0 °C to RT, 15.5 h, 90 %
Chemical structure
MeCd
PhH
Reflux, 90 min, 92 %
Chemical structure
+
Chemical structure
PhH, Et2O
RT, 60 min

See the Grignard Reaction
Chemical structure
Ac2O
AcOH
Reflux, 2.5 h
Chemical structure
H2, PtO2
AcOH
RT, 30 min, 14 % (3 steps)
Chemical structure
KOH
MeOH, H2O
Reflux, 2 h, 85 %
Chemical structure

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See : Org. Synth. 1937, 17, 43; Ber. 1935, 68, 2091; Helv. Chim. Acta 1938, 21, 866; J. Chem. Soc. 1950, 2325.
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