Synthesis of Cephalosporin C1

Structure of Cephalosporin C1

C16H21N3O8S

Principal investigatorRobert B. Woodward
Publication year1966
Synthesis typeTotal
Number of steps 19 (3 parts)
References
Part 1 of 3
intermediate structure
Phosgene, Pyr
CH2Cl2, t-BuOH
intermediate structure
CH2N2
intermediate structure + intermediate structure
105 °C, 45 h
intermediate structure
Pb(OAc)4
PhH
Reflux, 2 h
intermediate structure
NaOAc
MeOH
Reflux, 24 h
intermediate structure
MsCl, i-Pr2NEt
DMF
intermediate structure
NaN3
H2O
intermediate structure
Al(Hg)
MeOH
-15 °C, 24 h
intermediate structure
i-Bu3Al
PhMe
intermediate structure
Part 2 of 3
intermediate structure
Cl3CCH2OH, TsOH
PhMe
Reflux
intermediate structure
NaIO4
MeOH, H2O
intermediate structure + intermediate structure intermediate structure
Part 3 of 3
intermediate structure + intermediate structure
80 °C, 16 h
intermediate structure
CF3CO2H
RT, 2.5 h
intermediate structure intermediate structure + intermediate structure
DCC
THF
intermediate structure intermediate structure
DCC, Cl3CCH2OH
CH2Cl2, Pyr
intermediate structure intermediate structure
BH3.THF
THF
intermediate structure
Ac2O
Pyr
RT, 72 h
intermediate structure
Zn
AcOH
0 °C, 2.5 h
intermediate structure