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Named reactions

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Search synthesis

Taxol

"This communication is dedicated to the late Matthew Suffness, a pioneer in the development of Taxol."

Chemical structure of Taxol
C47H51NO14
Author Paul A. Wender
Publication year 1997
Synthesis type Formal synthesis
Number of steps 40 (linear)
References

Browse hundreds of other total syntheses.

Part 1 of 1
Chemical structure
KOt-Bu, PrenylBr
DME
-78 °C to RT, 4 h, 41 %

The yield was 82 % brsm.
Chemical structure
  1. O3
  2. Thiourea
CH2Cl2, MeOH
5 h, 85 %
Chemical structure
MeOH
0 °C, 3 h, 85 %
Chemical structure
  1. Ethyl propynoate, i-Pr2NLi
  2. TMSCl
THF
-78 to 0 °C, 89 %
Chemical structure
MeLi, CuI
Et2O
-78 °C to RT, ON, 97 %

See the Michael Addition
See the Aldol Addition
Chemical structure
(Ph3P)3RuCl2, NMO
Acetone
RT, 60 min, 95 %
Chemical structure
Reagent structure
TMS2NK
THF
-78 to -20 °C, 2 h, 56 %

97.5 % yield at 57 % conversion.
Chemical structure
LiAlH4
Et2O
-78 to 0 °C, 2.5 h, 74 %
Chemical structure
  1. TBSCl, Imidazole
  2. Pyr.TsOH, 2-Methoxypropene
CH2Cl2
0 °C to RT, 8 h, 91 %
Chemical structure
mCPBA, Na2CO3
CH2Cl2
-78 to -15 °C, 14 h

See the Prilezhaev Reaction
Chemical structure
DABCO ®, TIPSOTf, 2,6-Lutidine
CH2Cl2
-78 °C to Reflux, 14 h, 85 % (2 steps)

See the Grob Fragmentation
Chemical structure
O2, P(OEt)3, KOt-Bu
THF
-40 °C, 10 min, 74 %
Chemical structure
NaBH4
MeOH
RT, 90 min, 91 %
Chemical structure
Reagent structure
H2
1 atm
CH2Cl2
RT, 30 min, 92 %
Chemical structure
TMSCl, Triphosgene
Pyr
-78 °C to RT, 2 h, 95 %
Chemical structure
HCrO3Cl.Pyr
4 Å MS
CH2Cl2
RT, 2 h, 100 %
Chemical structure
Ph3P+CH2OMe Cl-, TMS2NK
THF
-78 °C to RT, 85 min, 91 %

See the Wittig Reaction
Chemical structure
HCl, NaI
Dioxane , H2O
RT, 18 h, 85 %

94 % yield based on 90 % conversion.
Chemical structure
TESCl, Pyr
CH2Cl2
-78 to -20 °C, 10 h, 92 %
Chemical structure
  1. Dess-Martin Periodinane, NaHCO3
  2. H2CN+Me2 I-, Et3N
CH2Cl2
RT, ON, 97 %

See the Mannich Reaction
Chemical structure
AllylMgBr, ZnCl2
THF
-78 °C, 17 min, 89 %

See the Grignard Reaction
Chemical structure
BnOCH2Cl, i-Pr2NEt
Sealed tube
CH2Cl2
60 °C, 72 h
Chemical structure
NH4F
MeOH
RT, 12 h, 93 % (2 steps)
Chemical structure
  1. PhLi
  2. Ac2O, Pyr, DMAP
THF
-78 °C to RT, 2.5 h, 79 %
Chemical structure
Reagent structure
CH2Cl2
80 min, 50 %

See the Lobry-de Bruyn-van Ekenstein Rearrangement
80 % yield based on 63 % conversion.
Chemical structure
  1. O3
  2. P(OEt)3
CH2Cl2
-78 °C to RT, 86 %
Chemical structure
ClCO2CH2CCl3, DMAP
CH2Cl2
RT, 42 h, 62 %

See the Aldol Addition
Chemical structure
HCl, NaI
Acetone, H2O
RT, 21 h, 65 %

97 % yield based on 67 % conversion.
Chemical structure
MsCl, DMAP
CH2Cl2, Pyr
0 °C, 3 h, 83 %
Chemical structure
LiBr
Acetone
RT, 72 h, 73 %

See the Finkelstein Reaction
79 % yield based on 94 % conversion.
Chemical structure
OsO4, Pyr
THF
RT, 23 h, 71 %

76 % yield based on 94 % conversion.
Chemical structure
Triphosgene, Pyr
CH2Cl2
0 °C, 30 min, 92 %
Chemical structure
KCN
EtOH
0 °C, 3 h, 68 %

76 % yield based on 89 % conversion.
Chemical structure
i-Pr2NEt
PhMe
Reflux, 9 h, 79 %

95 % yield based on 83 % conversion.
Chemical structure
Ac2O, DMAP
CH2Cl2
RT, ON, 89 %
Chemical structure
TASF
THF
0 °C, 5 min, 96 %
Chemical structure
PhLi
THF
-78 °C to RT, 15 min, 58 %

Also isolated was the C10-alcohol (30 % yield) which can be acetylated to the desired product.
Chemical structure

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Remaining...
54 % (3 steps)

See : Chem. Eur. J. 1999, 5, 121; Nature 1994, 367, 630.
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