Synthesis of Cephalosporin C1

Structure of Cephalosporin C1

C16H21N3O8S

Principal investigator	Robert B. Woodward
Publication year	1966
Synthesis type	Total
Number of steps	19 (3 parts)
References	J. Am. Chem. Soc. 1966, 88, 852.

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

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Part 2 of 3

intermediate structure

TsOH, Cl3CCH2OH

PhMe

Reflux

See the Fischer-Speier Esterification

intermediate structure

NaIO4

H2O, MeOH

intermediate structure

+

intermediate structure

H2O

See the Knoevenagel Condensation

intermediate structure

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Part 3 of 3

intermediate structure

+

intermediate structure

80 °C, 16 h

See the Michael Addition

intermediate structure

CF3CO2H

RT, 2.5 h

intermediate structure

intermediate structure

+

intermediate structure

DCC

THF

intermediate structure

intermediate structure

DCC, Cl3CCH2OH

CH2Cl2, Pyr

See the Steglich Esterification

intermediate structure

BH3.THF

THF

intermediate structure

Ac2O

Pyr

RT, 72 h

intermediate structure

Zn

AcOH

0 °C, 2.5 h

intermediate structure

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