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