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Named reactions

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Search synthesis

Taxol

Chemical structure of Taxol
C47H51NO14
Author Teruaki Mukaiyama
Publication year 1999
Synthesis type Total synthesis
Number of steps 61 (linear)
Reference

Browse hundreds of other total syntheses.

Part 1 of 1
Chemical structure
NaNO2, H2SO4
H2O
0 °C to RT, 5.5 d
Chemical structure
HC(OMe)3, H2SO4
MeOH
60 °C, 30 min, 88% (2 steps)
Chemical structure
TBSCl, Imidazole
DMF
0 °C, 6 h, 82%
Chemical structure
Cl3C(=NH)OBn, TfOH
Et2O
RT, 10 h, 100%
Chemical structure
i-Bu2AlH
Hexane(s)
-78 °C, 60 min, 95%
Chemical structure
i-PrCO2Me, i-Pr2NLi
Et2O
-78 °C, 65%

See the Aldol Addition
Also isolated was the C3-epimer (20 % yield).
Chemical structure
Cl3C(=NH)OCH2(p-MeOPh), TfOH
CH2Cl2
0 °C, 3 h, 75%

99 % yield based on 76 % conversion.
Chemical structure
i-Bu2AlH
Hexane(s)
-78 °C, 60 min, 92%
Chemical structure
DMSO, (COCl)2, Et3N
CH2Cl2
-78 °C to RT, 75 min, 97%

See the Swern Oxidation
Chemical structure + Chemical structure
MgBr2.OEt2
PhMe
-15 °C, 75 min, 71%

See the Mukaiyama Aldol Addition
87 % yield based on 88 % conversion. Also isolated was the C2-epimer (16 % yield).
Chemical structure
TBSOTf, 2,6-Lutidine
CH2Cl2
0 °C, 60 min, 100%
Chemical structure
i-Bu2AlH
PhMe
-78 °C, 60 min
Chemical structure
DMSO, (COCl)2, Et3N
CH2Cl2
-78 °C to RT, 75 min, 94% (2 steps)

See the Swern Oxidation
Chemical structure
MeMgBr
Et2O
-78 °C, 100 min, 99%

Selectivity : 75:25 dr
See the Grignard Reaction
Chemical structure
DMSO, (COCl)2, Et3N
CH2Cl2
-78 °C to RT, 45 min, 97%

See the Swern Oxidation
Chemical structure
  1. TMS2NLi
  2. TMSCl
THF
-78 °C, 90 min
Chemical structure
NBS
THF
0 °C, 30 min, 100% (2 steps)
Chemical structure
  1. TMS2NLi
  2. MeI
THF, HMPA
-78 °C, 2.5 h, 100%

Selectivity : 80:20 dr
Chemical structure
HCl
THF, H2O
0 °C, 60 min, 83%
Chemical structure
DMSO, (COCl)2, Et3N
CH2Cl2
-78 °C to RT, 75 min, 95%

See the Swern Oxidation
Chemical structure
SmI2
THF
-78 °C, 20 min, 70%

Selectivity : 83:17 dr
See the Reformatsky Reaction
Chemical structure
Ac2O, DMAP
Pyr
RT, 90 min, 87%
Chemical structure
DBU
PhH
60 °C, 90 min, 91%
Chemical structure + Chemical structure
t-BuLi, CuCN
Et2O
-78 to 0 °C, 2 h, 92%

See the Michael Addition
99 % yield base on 93 % conversion.
Chemical structure
HCl
THF, H2O
0 °C, 97%
Chemical structure
n-Pr4N+ RuO4-, NMO
4 Å MS
CH2Cl2
0 °C, 30 min, 92%

See the Ley-Griffith Oxidation
Chemical structure
NaOMe
MeOH, THF
0 °C, 90%

See the Aldol Addition
Also isolated was the C4-epimer (8 % yield).
Chemical structure
AlH3
PhMe, THF
-78 °C, 2 h, 94%
Chemical structure
2,2-Dimethoxypropane, Camphorsulfonic acid
CH2Cl2
RT, 60 min, 100%
Chemical structure
DDQ
CH2Cl2, H2O
RT, 60 min, 97%
Chemical structure
H2Cr2O7.2Pyr
CH2Cl2
RT, 16 h, 90%

94 % yield based on 96 % conversion.
Chemical structure
4-Iodobutene, s-BuLi
Cyclohexane, PhH
-23 to 0 °C, 85 min, 96%
Chemical structure
n-Bu4N+ F-
THF
50 °C, 60 min, 100%
Chemical structure
CyMeSiCl2, Imidazole
DMF
RT, 15 min, 99%
Chemical structure
MeLi
THF, HMPA
-78 °C, 30 min, 96%
Chemical structure
n-Pr4N+ RuO4-, NMO
4 Å MS
CH2Cl2, MeCN
0 °C to RT, 60 min, 80%

See the Ley-Griffith Oxidation
Chemical structure
PdCl2
DMF, H2O
RT, 3.5 h, 98%

See the Wacker Oxidation
Chemical structure
TiCl2, LiAlH4
THF
0 °C to Reflux, 40 min, 43-71%

See the Pinacol Coupling
Chemical structure
Na
NH3, THF
-78 to -45 °C, 2 h, 100%

See the Birch Reduction
Chemical structure
n-Bu4N+ F-
THF
RT, 5 min, 100%
Chemical structure
Triphosgene, Pyr
CH2Cl2
-45 °C, 70 min, 100%
Chemical structure
Ac2O, DMAP
PhH
0 to 35 °C, 10 h, 84%
Chemical structure
HCl
THF, H2O
60 °C, 10 h
Chemical structure
TESCl
Pyr
0 °C to RT, 40 min, 83% (2 steps)
Chemical structure
n-Pr4N+ RuO4-, NMO
4 Å MS
CH2Cl2
RT, 60 min, 76%

See the Ley-Griffith Oxidation
Chemical structure
TCDI, DMAP
PhMe
100 °C, 8 h
Chemical structure
P(OMe)3
110 °C, 5 h, 53% (2 steps)

See the Corey-Winter Olefin Synthesis
Chemical structure
HCrO3Cl.Pyr, NaOAc, Celite ®
PhH
95 °C, 7 h, 78%
Chemical structure
K(s-Bu)3BH
THF
-23 °C, 4 h, 87%
Chemical structure
TESOTf
Pyr
-23 °C, 10 min, 98%
Chemical structure
CuBr, BzOOt-Bu
Dark
MeCN
-23 to 50 °C, 14 h, 62%

See the Wohl-Ziegler Reaction
Also isolated was the desired exocyclic allylic bromide (15 % yield, see next step).
Chemical structure
CuBr
MeCN
50 °C, 100 min, 69%

The yield was 92 % yield brsm.
Chemical structure
OsO4, Pyr
Et2O, THF
RT, 17 h, 92%

96 % yield based on 96 % conversion.
Chemical structure
DBU
PhMe
50 °C, 105 min, 42%

81 % yield based on 52 % conversion.
Chemical structure
Ac2O, DMAP
Pyr
RT, 13 h, 91%
Chemical structure
PhLi
THF
-78 °C, 15 min, 94%
Chemical structure
Pyr.HF
THF
RT, 60 min, 96%
Chemical structure
TESCl
Pyr
RT, 30 min, 87%

92 % yield based on 95 % conversion.
Chemical structure + Chemical structure
DPTC, DMAP
PhMe
73 °C, 4 h, 66%
Chemical structure
H2, Pd(OH)2/C
1 atm
EtOH
RT, 23 h, 76%
Chemical structure
Pyr.HF
THF
RT, 72 h, 100%
Chemical structure

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