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Named reactions

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Search synthesis

Taxol

Chemical structure of Taxol
C47H51NO14
Author Isao Kuwajima
Publication year 1998
Synthesis type Total synthesis
Number of steps 66 (3 parts)
References

Browse hundreds of other total syntheses.

Part 1 of 3
Chemical structure
  1. i-Pr2NLi
  2. TESCl
THF
-78 °C, 30 min
Chemical structure
mCPBA, NaHCO3
CH2Cl2
0 °C, 30 min, 96 % (2 steps)

See the Rubottom Oxidation
Chemical structure
PhSCHLiOMe
THF
-78 °C, 2 h
Chemical structure
CuO, CuCl2
THF, MeOH
Reflux, 4 h, 54 % (2 steps)
Chemical structure
TsOH, BnOH
PhH
Reflux, 6 h
Chemical structure
CSCl2, DMAP
CH2Cl2
0 °C to RT, 30 min, 64 % (2 steps)
Chemical structure
Reagent structure
2,6-Di-tert-butylphenol
THF
RT, 48 h, 82 %

See the Corey-Winter Olefin Synthesis
Chemical structure

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Part 2 of 3
Chemical structure
  1. n-BuLi
  2. EtCOH
THF
-78 to 0 °C, 3 h
Chemical structure
H2, Lindlar Catalyst
1 atm
Hexane(s)
RT, 7 h
Chemical structure
DMSO, (COCl)2, Et3N
CH2Cl2
-78 °C to RT, 10 h

See the Swern Oxidation
Chemical structure
i-PrCO2Et, i-Pr2NLi
THF
-78 to 0 °C, 2.5 h

See the Michael Addition
Chemical structure
KOt-Bu
Et2O
0 °C, 3 h

See the Dieckmann Condensation
Chemical structure
t-BuCOCl, Et3N
CH2Cl2
RT, ON
Chemical structure
TsOH
MeOH
RT, 3 h, 52 % (7 steps)
Chemical structure
DMSO, (COCl)2, Et3N
CH2Cl2
-78 to 0 °C, ON, 92 %

See the Swern Oxidation
Chemical structure
TIPSOTf, DBU, DMAP
CH2Cl2
-78 °C to RT, 4 h, 71 %
Chemical structure
K2OsO2(OH)4, K3Fe(CN)6, K2CO3, DHQ-PHN
t-BuOH
0 °C, 11 h, 98 %

Selectivity : 96:04 er
See the Sharpless Asymmetric Dihydroxylation
Chemical structure
(CH2NHMe)2
Dean-Stark
PhH
Reflux, 30 min
Chemical structure
TIPSCl, KOMe
THF, Et3N
-23 °C, 6 h, 62 % (2 steps)
Chemical structure
(CH2NHMe)2
Dean-Stark
PhH
Reflux, 30 min
Chemical structure
PhSCHLiTMS
THF
-23 to 0 °C, 4 h, 64 % (2 steps)

See the Peterson Olefination
Chemical structure

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Part 3 of 3
Chemical structure
+
Chemical structure
t-BuMgCl
THF
-78 °C, 90 min, 68 %

See the Grignard Reaction
Chemical structure
(MeBO)3, Pyr
PhH
RT, 30 min, 77 %
Chemical structure
TiCl2(Oi-Pr)2
CH2Cl2
-78 to 0 °C, 90 min

See the Mukaiyama Aldol Addition
Chemical structure
Pinacol, DMAP
PhH
RT, 60 min, 59 % (2 steps)
Chemical structure
  1. n-BuLi
  2. t-Bu2SiHCl
THF
-78 to 0 °C, 2 h
Chemical structure
i-Bu2AlH
CH2Cl2
-78 °C, 60 min
Chemical structure
TBSOTf, 2,6-Lutidine
CH2Cl2
-23 °C, 30 min, 62 % (3 steps)
Chemical structure
O2, Tetraphenylporphyrin
CH2Cl2
RT, 7 h

See the Diels-Alder Reaction
Chemical structure
n-Bu3SnH, AIBN
PhH
Reflux, ON, 80 % (2 steps)
Chemical structure
H2, Pd(OH)2
1 atm
EtOH
RT, 4.5 h
Chemical structure
PhCH(OMe)2, Camphorsulfonic acid
CH2Cl2
-23 °C, ON, 79 % (2 steps)
Chemical structure
Et2Zn, CH2I2
PhMe
0 °C, 30 min, 66 %

See the Simmons-Smith Reaction
Chemical structure
Dess-Martin Periodinane
CH2Cl2
RT, ON, 77 %

See the Dess-Martin Oxidation
Chemical structure
H2, Pd(OH)2
1 atm
EtOH
RT, 30 min, 84 %
Chemical structure
Triphosgene, Pyr
CH2Cl2
-45 °C, 2 h
Chemical structure
n-Bu4N+ F-
THF
RT, 2.5 h, 95 % (2 steps)
Chemical structure
PhCH(OMe)2, Pyr.TsOH
PhH
Reflux, 60 min, 86 %
Chemical structure
K2CO3
MeOH, THF
RT, 60 min, 100 %
Chemical structure
SmI2
THF, HMPA
RT, 5 h, 100 %
Chemical structure
n-Bu4N+ F-, BHT
THF
RT, 3 h
Chemical structure
NaOMe, BHT
MeOH
RT, 60 h, 45 % (2 steps)
Chemical structure
PhB(OH)2
CH2Cl2
RT, 15 min
Chemical structure
TBSOTf, 2,6-Lutidine
CH2Cl2
-45 °C, 12 h
Chemical structure
H2O2, NaHCO3
EtOAc, H2O
RT, 60 min, 70 % (3 steps)
Chemical structure
Dess-Martin Periodinane
CH2Cl2
RT, 60 min, 92 %

See the Dess-Martin Oxidation
Chemical structure
2-Methoxypropene, Pyr.TsOH
CH2Cl2
RT, 5 min, 97 %
Chemical structure
  1. TMS2NK
  2. PhNTf2
THF
-78 °C, 60 min, 89 %
Chemical structure
TMSCH2MgCl, Pd(PPh3)4
Et2O
RT, 60 min, 91 %

See the Kumada-Corriu Coupling
Chemical structure
NCS
MeOH
RT, 10 h, 88 %
Chemical structure
  1. i-Pr2NLi
  2. MoOPH
THF
-23 °C, 30 min, 80 %
Chemical structure
Ac2O, DMAP
CH2Cl2
RT, 30 min, 92 %
Chemical structure
DBN
PhMe
Reflux, 10 h, 71 %
Chemical structure
OsO4, Pyr
Et2O
RT, 12 h, 86 %
Chemical structure
DBU
PhMe
Reflux, 4 h, 86 %
Chemical structure
Pyr.TsOH
MeOH
RT, 30 min
Chemical structure
TESCl, Imidazole, DMAP
DMF
RT, 5 h, 97 % (2 steps)
Chemical structure
H2, Pd(OH)2
EtOH
RT, 60 min, 97 %
Chemical structure
Triphosgene, Pyr
CH2Cl2
-78 to 0 °C, 60 min, 94 %
Chemical structure
Ac2O, DMAP
CH2Cl2
RT, 6 h, 66 %
Chemical structure
PhLi
THF
-78 °C, 83 %
Chemical structure
Pyr.HF
THF
RT, 2 h, 88 %
Chemical structure
ClCO2CH2CCl3, Pyr
CH2Cl2
RT, 3 h, 94 %
Chemical structure
TASF
THF
RT, 48 h, 80 %
Chemical structure
+
Chemical structure
TMS2NLi
THF
-78 to 0 °C, 30 min, 77 %
Chemical structure
Zn
AcOH, H2O
RT, 16 h, 84 %
Chemical structure

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