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Named reactions

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Search synthesis

Taxol

Chemical structure of Taxol
C47H51NO14
Author Kyriacos C. Nicolaou
Publication year 1994
Synthesis type Total synthesis
Number of steps 40 (3 parts)
References

Browse hundreds of other total syntheses.

Part 1 of 3
Chemical structure
2-Chloroacrylonitrile
Sealed tube
PhH
130 °C, 72 h, 85 %

See the Diels-Alder Reaction
Chemical structure
KOH
t-BuOH
65 °C, 3 h, 50 %
Chemical structure
TBSCl
CH2Cl2
RT, 60 min, 100 %
Chemical structure
+
Chemical structure
THF
RT, 3 h, 80 %
Chemical structure

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Part 2 of 3
Chemical structure
+
Chemical structure
PhB(OH)2, Neopentyl glycol
Dean-Stark
PhH
RT to Reflux, 48.5 h, 61 %

See the Diels-Alder Reaction
Chemical structure
TBSOTf, 2,6-Lutidine, DMAP
CH2Cl2
0 °C, 4 h, 95 %
Chemical structure
LiAlH4
Et2O
0 °C, 60 min, 94 %
Chemical structure
Camphorsulfonic acid
MeOH
RT, 60 min, 90 %
Chemical structure
TBDPSCl, Imidazole
DMF
RT, 6 h, 92 %
Chemical structure
BnBr, KH, n-Bu4N+ I-
Et2O
RT, 2 h, 87 %

See the Williamson Ether Synthesis
Chemical structure
LiAlH4
Et2O
RT, 12 h, 80 %
Chemical structure
2,2-Dimethoxypropane, Camphorsulfonic acid
CH2Cl2
RT, 7 h, 82 %
Chemical structure
n-Pr4N+ RuO4-, NMO
MeCN
RT, 2 h, 95 %

See the Ley-Griffith Oxidation
Chemical structure

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Part 3 of 3
Chemical structure
+
Chemical structure
n-BuLi
THF
-78 °C to RT, 30 min, 82 %

See the Shapiro Reaction
Chemical structure
VO(acac)2, t-BuOOH
4 Å MS
PhH
RT, 12 h, 87 %
Chemical structure
LiAlH4
Et2O
RT, 7 h, 76 %
Chemical structure
KH, COCl2
Et2O, HMPA
RT, 2 h, 48 %
Chemical structure
n-Bu4N+ F-
THF
RT, 7 h, 80 %
Chemical structure
n-Pr4N+ RuO4-, NMO
MeCN, CH2Cl2
RT, 2 h, 82 %

See the Ley-Griffith Oxidation
Chemical structure
(TiCl3)2.2DME, Zn-Cu
DME
70 °C, 60 min, 23 %

See the Pinacol Coupling
Chemical structure
+
Chemical structure
43 %

Also isolated was the correponding diastereoisomer (43% yield).
Chemical structure
K2CO3
MeOH
90 %
Chemical structure
Ac2O, DMAP
CH2Cl2
RT, 2 h, 95 %
Chemical structure
n-Pr4N+ RuO4-, NMO
MeCN
RT, 2 h, 93 %

See the Ley-Griffith Oxidation
Chemical structure
BH3.THF, H2O2
THF, H2O
0 °C, 2.5 h, 55 %
Chemical structure
HCl
MeOH, H2O
RT, 5 h, 80 %
Chemical structure
Ac2O, DMAP
CH2Cl2
RT, 30 min, 95 %
Chemical structure
H2, Pd/C
EtOAc
RT, 30 min, 97 %
Chemical structure
TESCl
Pyr
RT, 12 h, 85 %
Chemical structure
K2CO3
MeOH
0 °C, 15 min, 95 %
Chemical structure
TMSCl, Pyr
CH2Cl2
0 °C, 15 min, 96 %
Chemical structure
Tf2O, i-Pr2NEt
CH2Cl2
RT, 30 min, 70 %
Chemical structure
Camphorsulfonic acid
MeOH
10 min
Chemical structure
SiO2
CH2Cl2
4 h, 60 % (2 steps)
Chemical structure
Ac2O, DMAP
CH2Cl2
RT, 4 h, 94 %
Chemical structure
PhLi
THF
-78 °C, 10 min, 80 %
Chemical structure
HCrO3Cl.Pyr, NaOAc, Celite ®
PhH
Reflux, 60 min, 75 %
Chemical structure
NaBH4
MeOH
RT, 5 h, 83 %
Chemical structure
+
Chemical structure
TMS2NNa
THF
0 °C, 78 %

87 % yield at 90 % conversion.
Chemical structure
Pyr.HF
THF
RT, 90 min, 80 %
Chemical structure

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