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Named reactions

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Search synthesis

Taxol

Chemical structure of Taxol
C47H51NO14
Author Robert A. Holton
Publication year 1994
Synthesis type Total synthesis
Number of steps 46 (linear)
References

Browse hundreds of other total syntheses.

Part 1 of 1
Chemical structure
t-BuLi
Hexane(s)
Reflux, 5 h
Chemical structure
t-BuOOH, Ti(Oi-Pr)4
CH2Cl2
RT, 2 h, 98% (2 steps)
Chemical structure
BF3.OEt2, TfOH
CH2Cl2
-80 °C, 22 h, 70%

93 % yield at 75 % conversion
Chemical structure
TESCl, DMAP
CH2Cl2, Et3N
RT, 105 min
Chemical structure
t-BuOOH, Ti(Oi-Pr)4
CH2Cl2
0 °C to Reflux, 9.5 h

See the Grob Fragmentation
Chemical structure
TBSOTf
Pyr
-23 to 0 °C, 105 min, 94% (3 steps)
Chemical structure + Chemical structure
i-Pr2NMgBr
THF
-23 °C to RT, 2.5 h

See the Aldol Addition
Chemical structure
COCl2, Pyr
CH2Cl2, EtOH
-23 to -10 °C, 60 min, 75% (2 steps)
Chemical structure
Reagent structure
i-Pr2NLi
THF
-78 to -35 °C, 70 min, 85%

See the Davis Asymmetric Hydroxylation
Chemical structure
Red-Al
PhMe
-78 °C to RT, 12 h
Chemical structure
COCl2, Pyr
PhMe
-78 °C to RT, 60 min, 97% (2 steps)
Chemical structure
(COCl)2, DMSO, Et3N
CH2Cl2
-78 °C to RT, 30 min, 95%

See the Swern Oxidation
Chemical structure
LiTMP
THF
-23 to -10 °C, 30 min, 90%

See the Chan Rearrangement
Chemical structure
SmI2
THF
RT, 4 h, 92%

Selectivity : 84:16 R/S
Chemical structure
Reagent structure
LiTMP
THF
-40 to -10 °C, 50 min, 88%

Also isolated was the C3-epimer (8% yield).
Chemical structure
Red-Al
PhMe
-78 °C, 90 min, 88%
Chemical structure
COCl2, Pyr
PhMe
-78 to -23 °C, 30 min, 100%
Chemical structure
  1. O3
  2. P(OMe)3, Et3N
CH2Cl2, MeOH
-78 to 0 °C
Chemical structure
KMnO4, KH2PO4
t-BuOH, Acetone, H2O
0 °C, 30 min
Chemical structure
CH2N2
Et2O
RT, 93% (3 steps)
Chemical structure
i-Pr2NLi
THF
-78 °C, 40 min, 84%

See the Dieckmann Condensation
Chemical structure
2-Methoxypropene, TsOH
THF
0 °C, 10 min, 100%
Chemical structure
KSPh, PhSH
DMF
86 °C, 3.5 h, 92%
Chemical structure
Pyr.TsOH
THF, CH2Cl2
RT, 3 h, 92%
Chemical structure
BnOCH2Cl, i-Pr2NEt, n-Bu4N+ I-
CH2Cl2
Reflux, 32 h, 92%
Chemical structure
  1. i-Pr2NLi
  2. TMSCl
THF, Et3N
-78 °C, 25 min, 99%
Chemical structure
mCPBA
Hexane(s)
RT, 5 h, 74%

See the Rubottom Oxidation
Chemical structure
MeMgBr
CH2Cl2
-65 to -48 °C, 16.5 h, 95%

See the Grignard Reaction
Chemical structure
Reagent structure
PhMe
Reflux, 20 min

See the Burgess Dehydration
Chemical structure
HF, Pyr
MeCN, H2O
0 °C, 20 min, 63% (2 steps)
Chemical structure
OsO4, Pyr
Et2O, THF
0 °C, 12 h, 80%
Chemical structure
TMSCl, Et3N
CH2Cl2
-78 °C, 60 min
Chemical structure
  1. i-Pr2NLi
  2. TsCl
THF
-78 to -35 °C, 3.5 h
Chemical structure
HF, Pyr
MeCN, H2O
0 °C, 15 min, 80% (3 steps)
Chemical structure
DBU
PhMe
80 to 110 °C, 80 min, 85%
Chemical structure
Ac2O, DMAP
Pyr
RT, 25 h, 72%
Chemical structure
Pyr.HF
MeCN
0 °C, 11 h, 100%
Chemical structure
PhLi
THF
-78 °C, 10 min, 85%
Chemical structure
n-Pr4N+ RuO4-, NMO
CH2Cl2
RT, 15 min, 100%

See the Ley-Griffith Oxidation
Chemical structure
(PhSeO)2O, KOt-Bu
THF
-78 to 0 °C, 80 min
Chemical structure
KOt-Bu
THF
-78 °C, 10 min

See the Lobry-de Bruyn-van Ekenstein Rearrangement
Chemical structure
Ac2O, DMAP
Pyr
RT, 19 h, 100% (3 steps)
Chemical structure
TASF
THF
RT, 15 min, 94%
Chemical structure + Chemical structure
TMS2NLi
THF
-45 to 0 °C, 2 h
Chemical structure
HF, Pyr
MeCN, H2O
0 °C, 60 min, 99% (2 steps)
Chemical structure
H2, Pd/C
1 atm
EtOH
Reflux, 45 min, 94%
Chemical structure

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