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6-Demethyl-6-deoxytetracycline

Chemical structure of 6-Demethyl-6-deoxytetracycline
C21H22N2O7
Author Robert B. Woodward
Publication year 1962
Synthesis type Total synthesis
Number of steps 24 (linear)
References

Browse hundreds of other total syntheses.

Part 1 of 1
Chemical structure
  1. NaH, MeOAc
  2. ClCH2CO2Me
DMF
50-60 °C, 4.5 h, 55%

See the Claisen Condensation
Chemical structure
Methyl acrylate, Me3N+Bn HO-
Dioxane
50-70 °C, 60 min, 88%

See the Michael Addition
Chemical structure
H2SO4
AcOH, H2O
Reflux, 24 h
Chemical structure
H2SO4
MeOH, CHCl3
Reflux, 24 h, 44% (2 steps)

See the Fischer Esterification
Chemical structure
H2, Pd/C
14 atm
AcOH
30 °C, 2 h
Chemical structure
H2SO4
MeOH, CHCl3
Reflux, 24 h, 69% (2 steps)

See the Fischer Esterification
This step was required for purification purposes (3.3 kg scale!)
Chemical structure
NaOH
H2O
100 °C, 18 h
Chemical structure
Cl2, I2
AcOH
12-17 °C, 7.5 h
Chemical structure
HF
H2O
15 °C, 18 h, 63% (3 steps)
Chemical structure
H2SO4
MeOH, CHCl3
Reflux, 20 h, 66%

See the Fischer Esterification
Chemical structure
(CO2Me)2, NaH
DMF, MeOH
35-80 °C, 44%

See the Claisen Condensation
See the Dieckmann Condensation
Chemical structure
HCl
AcOH, H2O
90-94 °C, 45 min, 73%
Chemical structure + Chemical structure
Mg(OMe)2
PhMe
Reflux, 2.5 h, 52%

See the Claisen-Schmidt Condensation
Chemical structure
Me2NH
H2O
0 °C, 2 h

See the Michael Addition
Chemical structure
NaBH4
DME, H2O
-78 to °C, 30 min, 53% (2 steps)
Chemical structure
TsOH
Dean-Stark
PhMe
Reflux, 3 h, 90%

See the Fischer Esterification
Chemical structure
Zn
HCO2H
RT, 1 min, 81%
Chemical structure
H2, Pd/C
3 atm
EtOH, Et3N
RT, 3 h, 91%
Chemical structure
ClCO2i-Pr, Et3N
CHCl3
0 °C, 30 min
Chemical structure + Chemical structure
MeCN
RT, ON
Chemical structure
NaH
MeOH, DMF
RT to 155 °C, 20 min

See the Dieckmann Condensation
Chemical structure
HBr
H2O
100 °C, 20 min, 9-15% (4 steps)

Yield BRSM
Chemical structure
O2, CeCl3.7H2O
DMF, MeOH, Buffer (pH = 10.4)
RT, 15 min
Chemical structure
HCl, CaCl2
n-BuOH, H2O, Ethanolamine
Reflux, 3.5 h, 6% (2 steps)
Chemical structure

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