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Named reactions

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Search synthesis

Taxol

"We dedicate this work to Dr. Monroe Wall of the Research Triangle Institute for his discovery of taxol and many other fascinating Natural Products."

Chemical structure of Taxol
C47H51NO14
Author Samuel J. Danishefsky
Publication year 1996
Synthesis type Formal synthesis
Number of steps 53 (2 parts)
Reference

Browse hundreds of other total syntheses.

Part 1 of 2
Chemical structure
NH2NH2, Et3N
EtOH
RT, 90 min, 72%
Chemical structure
I2, DBN
THF
RT, 45 min, 52%

See the Barton Vinyl Iodide Synthesis
Chemical structure
I2, DBN
THF
0 °C to RT, 8.5 h, 89%
Chemical structure
TMSCN, KCN, 18-Crown-6
CH2Cl2
0 °C to RT, 8 h, 89%
Chemical structure

Report an error in this part

Part 2 of 2
Chemical structure
NaBH4
EtOH
0 °C, 97%
Chemical structure
Ac2O, DMAP
CH2Cl2, Pyr
0 °C, 99%
Chemical structure
(CH2OH)2, Naphthalenesulfonic Acid
Dean-Stark
PhH
Reflux, 70%
Chemical structure
NaOMe
MeOH, THF
98%
Chemical structure
TBSOTf, 2,6-Lutidine
CH2Cl2
0 °C, 97%
Chemical structure
BH3.THF, H2O2, NaOH
THF, H2O
0 °C to RT, 17 h
Chemical structure
H2Cr2O7.2Pyr
4 Å MS
CH2Cl2
0 °C to RT, 10.5 h
Chemical structure
NaOMe
MeOH
RT, 10 h, 62% (3 steps)
Chemical structure
Me3S+ I-, TMS2NK
THF
0 °C, 2.5 h, 99%

See the Johnson-Corey-Chaykovsky Reaction
Chemical structure
Al(Oi-Pr)3
PhMe
Reflux, 38 h, 99%
Chemical structure
OsO4, NMO
Acetone, i-PrOH, H2O
RT, 15 h, 66%

See the Upjohn Dihydroxylation
Chemical structure
TMSCl, Tf2O, Pyr
CH2Cl2, Ethylene Glycol
-78 °C to Reflux, 69%
Chemical structure
BnBr, NaH, n-Bu4N+ I-
THF
0 °C to RT, 4.5 h, 98%

See the Williamson Ether Synthesis
Chemical structure
TsOH
Acetone, H2O
Reflux, 2.5 h, 84%
Chemical structure
TMSOTf, Et3N
CH2Cl2
-78 °C, 4 h
Chemical structure
DMDO
CH2Cl2
0 °C, 10 min
Chemical structure
Camphorsulfonic acid
Acetone
RT, 30 min, 89% (3 steps)

See the Rubottom Oxidation
Chemical structure
Pb(OAc)4
PhH, MeOH
0 °C, 10 min, 97%

See the Criegee Reaction
Chemical structure
CTPS
MeOH
Reflux, 10 h, 97%
Chemical structure
LiAlH4
THF
0 °C, 60 min, 100%
Chemical structure
o-NO2PhSeCN, n-Bu3P
THF
RT, 15 min, 88%
Chemical structure
H2O2
THF
RT, 12 h, 90%

See the Grieco Dehydration
Chemical structure
  1. O3
  2. Ph3P
CH2Cl2
-78 °C, 79%
Chemical structure + Chemical structure
t-BuLi
THF
-78 °C, 55 min, 93%
Chemical structure
n-Bu4N+ F-
THF
-78 °C, 15 min, 80%
Chemical structure
mCPBA, NaHCO3
CH2Cl2
RT, 11 h, 80%

See the Prilezhaev Reaction
Chemical structure
H2, Pd/C
1 atm
EtOH
-5 °C, 65%
Chemical structure
CDI, NaH
DMF
RT, 20 min, 81%
Chemical structure
Li(s-Bu)3BH
THF
-78 °C, 75 min, 93%
Chemical structure
  1. TMS2NK
  2. PhNTf2
THF
-78 °C, 10 min, 98%
Chemical structure
Pyr.TsOH
Acetone, H2O
75 °C, 9 h, 96%
Chemical structure
Ph3P=CH2
THF
-78 to 0 °C, 25 min, 77%

See the Wittig Reaction
Chemical structure
Pd(PPh3)4, K2CO3
MeCN
90 °C, 46%

See the Heck Coupling
Chemical structure
n-Bu4N+ F-
THF
RT, 8 h, 92%
Chemical structure
TESOTf, Et3N
CH2Cl2
-78 °C, 30 min, 92%
Chemical structure
mCPBA, NaHCO3
CH2Cl2
RT, 10.5 h, 45%

See the Prilezhaev Reaction
Chemical structure
H2, Pd/C
1 atm
EtOH
RT, 10 h, 82%
Chemical structure
Ac2O, DMAP
Pyr
RT, 16 h, 66%
Chemical structure
PhLi
THF
-78 °C, 2 min, 93%
Chemical structure
OsO4
Pyr
105 °C, 24 h
Chemical structure
Pb(OAc)4
PhH, MeOH
0 °C, 5 min, 61% (2 steps)

See the Criegee Reaction
Chemical structure
SmI2, Ac2O
THF
-78 °C, 10 min, 92%
Chemical structure
(PhSeO)2O, KOt-Bu
THF
-78 to 0 °C, 90 min
Chemical structure
KOt-Bu
THF
-78 °C, 10 min, 81% (2 steps)

See the Lobry-de Bruyn-van Ekenstein Rearrangement
Chemical structure
Ac2O, DMAP
Pyr
RT, 16 h, 76%
Chemical structure
HCrO3Cl.Pyr, NaOAc
PhH
Reflux, 60 min, 64%
Chemical structure
NaBH4
MeOH
RT, 2 h, 79%
Chemical structure

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Remaining...
63% (2 steps)

See : Nature 1994, 367, 630.
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