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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
i-Pr2NLi, TESCl
THF
-78 °C, 30 min
-78 °C, 30 min
PhSCHLiOMe
THF
-78 °C, 2 h
-78 °C, 2 h
CuO, CuCl2
THF, MeOH
Reflux, 4 h, 54 % (2 steps)
Reflux, 4 h, 54 % (2 steps)
TsOH, BnOH
PhH
Reflux, 6 h
Reflux, 6 h
CSCl2, DMAP
CH2Cl2
0 °C to RT, 30 min, 64 % (2 steps)
0 °C to RT, 30 min, 64 % (2 steps)
Part 2 of 3
n-BuLi, EtCOH
THF
-78 to 0 °C, 3 h
-78 to 0 °C, 3 h
H2, Lindlar Catalyst
1 atm
Hexane(s)
RT, 7 h
1 atm
RT, 7 h
t-BuCOCl, Et3N
CH2Cl2
RT, ON
RT, ON
TsOH
MeOH
RT, 3 h, 52 % (7 steps)
RT, 3 h, 52 % (7 steps)
TIPSOTf, DBU, DMAP
CH2Cl2
-78 °C to RT, 4 h, 71 %
-78 °C to RT, 4 h, 71 %
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
0 °C, 11 h, 98 %
Selectivity : 96:04 er
See the Sharpless Asymmetric Dihydroxylation
(CH2NHMe)2
Dean-Stark
PhH
Reflux, 30 min
Dean-Stark
Reflux, 30 min
TIPSCl, KOMe
THF, Et3N
-23 °C, 6 h, 62 % (2 steps)
-23 °C, 6 h, 62 % (2 steps)
(CH2NHMe)2
Dean-Stark
PhH
Reflux, 30 min
Dean-Stark
Reflux, 30 min
Part 3 of 3
+ 
(MeBO)3, Pyr
PhH
RT, 30 min, 77 %
RT, 30 min, 77 %
Pinacol, DMAP
PhH
RT, 60 min, 59 % (2 steps)
RT, 60 min, 59 % (2 steps)
n-BuLi, t-Bu2SiHCl
THF
-78 to 0 °C, 2 h
-78 to 0 °C, 2 h
i-Bu2AlH
CH2Cl2
-78 °C, 60 min
-78 °C, 60 min
TBSOTf, 2,6-Lutidine
CH2Cl2
-23 °C, 30 min, 62 % (3 steps)
-23 °C, 30 min, 62 % (3 steps)
n-Bu3SnH, AIBN
PhH
Reflux, ON, 80 % (2 steps)
Reflux, ON, 80 % (2 steps)
H2, Pd(OH)2
1 atm
EtOH
RT, 4.5 h
1 atm
RT, 4.5 h
PhCH(OMe)2, Camphorsulfonic acid
CH2Cl2
-23 °C, ON, 79 % (2 steps)
-23 °C, ON, 79 % (2 steps)
H2, Pd(OH)2
1 atm
EtOH
RT, 30 min, 84 %
1 atm
RT, 30 min, 84 %
Triphosgene, Pyr
CH2Cl2
-45 °C, 2 h
-45 °C, 2 h
n-Bu4N+ F-
THF
RT, 2.5 h, 95 % (2 steps)
RT, 2.5 h, 95 % (2 steps)
PhCH(OMe)2, Pyr.TsOH
PhH
Reflux, 60 min, 86 %
Reflux, 60 min, 86 %
K2CO3
MeOH, THF
RT, 60 min, 100 %
RT, 60 min, 100 %
SmI2
THF, HMPA
RT, 5 h, 100 %
RT, 5 h, 100 %
n-Bu4N+ F-, BHT
THF
RT, 3 h
RT, 3 h
NaOMe, BHT
MeOH
RT, 60 h, 45 % (2 steps)
RT, 60 h, 45 % (2 steps)
PhB(OH)2
CH2Cl2
RT, 15 min
RT, 15 min
TBSOTf, 2,6-Lutidine
CH2Cl2
-45 °C, 12 h
-45 °C, 12 h
H2O2, NaHCO3
EtOAc, H2O
RT, 60 min, 70 % (3 steps)
RT, 60 min, 70 % (3 steps)
2-Methoxypropene, Pyr.TsOH
CH2Cl2
RT, 5 min, 97 %
RT, 5 min, 97 %
TMS2NK, PhNTf2
THF
-78 °C, 60 min, 89 %
-78 °C, 60 min, 89 %
NCS
MeOH
RT, 10 h, 88 %
RT, 10 h, 88 %
i-Pr2NLi, MoOPH
THF
-23 °C, 30 min, 80 %
-23 °C, 30 min, 80 %
Ac2O, DMAP
CH2Cl2
RT, 30 min, 92 %
RT, 30 min, 92 %
DBN
PhMe
Reflux, 10 h, 71 %
Reflux, 10 h, 71 %
OsO4, Pyr
Et2O
RT, 12 h, 86 %
RT, 12 h, 86 %
DBU
PhMe
Reflux, 4 h, 86 %
Reflux, 4 h, 86 %
Pyr.TsOH
MeOH
RT, 30 min
RT, 30 min
TESCl, Imidazole, DMAP
DMF
RT, 5 h, 97 % (2 steps)
RT, 5 h, 97 % (2 steps)
H2, Pd(OH)2
EtOH
RT, 60 min, 97 %
RT, 60 min, 97 %
Triphosgene, Pyr
CH2Cl2
-78 to 0 °C, 60 min, 94 %
-78 to 0 °C, 60 min, 94 %
Ac2O, DMAP
CH2Cl2
RT, 6 h, 66 %
RT, 6 h, 66 %
PhLi
THF
-78 °C, 83 %
-78 °C, 83 %
Pyr.HF
THF
RT, 2 h, 88 %
RT, 2 h, 88 %
ClCO2CH2CCl3, Pyr
CH2Cl2
RT, 3 h, 94 %
RT, 3 h, 94 %
TASF
THF
RT, 48 h, 80 %
RT, 48 h, 80 %
+ 
TMS2NLi
THF
-78 to 0 °C, 30 min, 77 %
-78 to 0 °C, 30 min, 77 %
Zn
AcOH, H2O
RT, 16 h, 84 %
RT, 16 h, 84 %
