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Taxol

Chemical structure of Taxol

Author	Kyriacos C. Nicolaou
Publication year	1994
Synthesis type	Total synthesis
Number of steps	40 (3 parts)
References	Nature 1994, 367, 630. J. Am. Chem. Soc. 1994, 116, 591. J. Chem. Soc., Chem. Commun. 1993, 1024. J. Chem. Soc., Chem. Commun. 1992, 1117. J. Chem. Soc., Chem. Commun. 1992, 1118.

Browse hundreds of other total syntheses.

Part 1 of 3

Chemical structure

2-Chloroacrylonitrile
Sealed tube

PhH
130 °C, 72 h, 85 %

See the Diels-Alder Reaction

Chemical structure

KOH

t-BuOH
65 °C, 3 h, 50 %

Chemical structure

TBSCl

CH₂Cl₂
RT, 60 min, 100 %

Chemical structure

+

Chemical structure

THF
RT, 3 h, 80 %

Chemical structure

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Part 2 of 3

Chemical structure

+

Chemical structure

PhB(OH)₂, Neopentyl glycol
Dean-Stark

PhH
RT to Reflux, 48.5 h, 61 %

See the Diels-Alder Reaction

Chemical structure

TBSOTf, 2,6-Lutidine, DMAP

CH₂Cl₂
0 °C, 4 h, 95 %

Chemical structure

LiAlH₄

Et₂O
0 °C, 60 min, 94 %

Chemical structure

Camphorsulfonic acid

MeOH
RT, 60 min, 90 %

Chemical structure

TBDPSCl, Imidazole

DMF
RT, 6 h, 92 %

Chemical structure

BnBr, KH, n-Bu₄N⁺ I^-

Et₂O
RT, 2 h, 87 %

See the Williamson Ether Synthesis

Chemical structure

LiAlH₄

Et₂O
RT, 12 h, 80 %

Chemical structure

2,2-Dimethoxypropane, Camphorsulfonic acid

CH₂Cl₂
RT, 7 h, 82 %

Chemical structure

n-Pr₄N⁺ RuO₄^-, NMO

MeCN
RT, 2 h, 95 %

See the Ley-Griffith Oxidation

Chemical structure

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Part 3 of 3

Chemical structure

+

Chemical structure

n-BuLi

THF
-78 °C to RT, 30 min, 82 %

See the Shapiro Reaction

Chemical structure

VO(acac)₂, t-BuOOH
4 Å MS

PhH
RT, 12 h, 87 %

Chemical structure

LiAlH₄

Et₂O
RT, 7 h, 76 %

Chemical structure

KH, COCl₂

Et₂O, HMPA
RT, 2 h, 48 %

Chemical structure

n-Bu₄N⁺ F^-

THF
RT, 7 h, 80 %

Chemical structure

n-Pr₄N⁺ RuO₄^-, NMO

MeCN, CH₂Cl₂
RT, 2 h, 82 %

See the Ley-Griffith Oxidation

Chemical structure

(TiCl₃)₂^.2DME, Zn-Cu

DME
70 °C, 60 min, 23 %

See the Pinacol Coupling

Chemical structure

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Chemical structure

43 %

Also isolated was the correponding diastereoisomer (43% yield).

Chemical structure

K₂CO₃

MeOH
90 %

Chemical structure

Ac₂O, DMAP

CH₂Cl₂
RT, 2 h, 95 %

Chemical structure

n-Pr₄N⁺ RuO₄^-, NMO

MeCN
RT, 2 h, 93 %

See the Ley-Griffith Oxidation

Chemical structure

BH₃^.THF, H₂O₂

THF, H₂O
0 °C, 2.5 h, 55 %

Chemical structure

HCl

MeOH, H₂O
RT, 5 h, 80 %

Chemical structure

Ac₂O, DMAP

CH₂Cl₂
RT, 30 min, 95 %

Chemical structure

H₂, Pd/C

EtOAc
RT, 30 min, 97 %

Chemical structure

TESCl

Pyr
RT, 12 h, 85 %

Chemical structure

K₂CO₃

MeOH
0 °C, 15 min, 95 %

Chemical structure

TMSCl, Pyr

CH₂Cl₂
0 °C, 15 min, 96 %

Chemical structure

Tf₂O, i-Pr₂NEt

CH₂Cl₂
RT, 30 min, 70 %

Chemical structure

Camphorsulfonic acid

MeOH
10 min

Chemical structure

SiO₂

CH₂Cl₂
4 h, 60 % (2 steps)

Chemical structure

Ac₂O, DMAP

CH₂Cl₂
RT, 4 h, 94 %

Chemical structure

PhLi

THF
-78 °C, 10 min, 80 %

Chemical structure

HCrO₃Cl^.Pyr, NaOAc, Celite ®

PhH
Reflux, 60 min, 75 %

Chemical structure

NaBH₄

MeOH
RT, 5 h, 83 %

Chemical structure

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Chemical structure

TMS₂NNa

THF
0 °C, 78 %

87 % yield at 90 % conversion.

Chemical structure

Pyr^.HF

THF
RT, 90 min, 80 %

Chemical structure

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