Synthesis of Cephalosporin C1

C16H21N3O8S
Principal investigator | Robert B. Woodward |
---|---|
Publication year | 1966 |
Synthesis type | Total |
Number of steps | 19 (3 parts) |
References |
Part 1 of 3
+

Phosgene,
Pyr
CH2Cl2, t-BuOH

CH2N2


105 °C, 45 h

Pb(OAc)4
PhH
Reflux, 2 h

NaOAc
MeOH
Reflux, 24 h

MsCl,
i-Pr2NEt
DMF

NaN3
H2O

Al(Hg)
MeOH
-15 °C, 24 h

i-Bu3Al
PhMe

Part 2 of 3
+


NaIO4
H2O, MeOH



Part 3 of 3
+
+



CF3CO2H
RT, 2.5 h



DCC
THF



BH3.THF
THF

Ac2O
Pyr
RT, 72 h

Zn
AcOH
0 °C, 2.5 h
