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Named reactions

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Search synthesis

Erythromycin A

Chemical structure of Erythromycin_A
C38H69NO12
Author Robert B. Woodward
Publication year 1981
Synthesis type Total synthesis
Number of steps 50 (4 parts)
References

Browse hundreds of other total syntheses.

Part 1 of 4
Chemical structure
+
Chemical structure
NaH
THF, DMSO
RT
Chemical structure
AcOH
H2O
RT
Chemical structure
D-Proline
MeCN
RT

See the Aldol Addition
Also isolated was the C6-epimer (50:50 dr). Both diastereoisomers were obtained as an enantioenriched mixture (36 % ee).
Chemical structure
MsCl
Pyr
RT
Chemical structure
Al2O3
EtOAc
RT, 12% (5 steps)

The product was cristallized to optical purity from the enantioenriched mixture.
Chemical structure
NaBH4
MeOH
0 °C
Chemical structure
  1. KH
  2. MeOCH2I
THF
0 °C
Chemical structure
OsO4
Et2O
RT
Chemical structure
Me2C(OMe)2, TsOH
CH2Cl2
0 °C, 74% (4 steps)
Chemical structure

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Part 2 of 4
Chemical structure
CF3CO2H
CH2Cl2
RT
Chemical structure
(CF3CO)2O, DMSO, i-Pr2NEt
CH2Cl2
-60 to 0 °C, 85% (2 steps)

See the Swern Oxidation
Chemical structure

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Part 3 of 4
Chemical structure
Ni (Raney)
EtOH
Reflux
Chemical structure
  1. o-NO2PhSeCN, n-Bu3P
  2. H2O2, H2O
THF
RT

See the Grieco Dehydration
Chemical structure
  1. O3
  2. Me2S
CH2Cl2, MeOH
-78 °C to RT, 80% (3 steps)
Chemical structure

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Part 4 of 4
Chemical structure
+
Chemical structure
MesLi
THF
-50 °C

See the Aldol Addition
Chemical structure
(CF3CO)2O, DMSO, i-Pr2NEt
CH2Cl2
-60 to 0 °C, 76% (2 steps)

See the Swern Oxidation
Chemical structure
  1. KH
  2. AcCl
THF, HMPA
-78 to 0 °C
Chemical structure
NaBH4
MeOH
-20 °C
Chemical structure
MsCl, DMAP
MeOH, Pyr
0 °C
Chemical structure
BnSH, n-BuLi
THF
-50 °C, 85% (4 steps)

See the Michael Addition
Chemical structure
LiAlH4
Et2O
-20 °C
Chemical structure
Ac2O, DMAP
CH2Cl2
0 °C, 92% (2 steps)
Chemical structure
Ni (Raney)
EtOH, DMF
Reflux
Chemical structure
  1. o-NO2PhSeCN, n-Bu3P
  2. H2O2, H2O
THF
RT

See the Grieco Dehydration
Chemical structure
  1. O3
  2. Me2S
CH2Cl2, MeOH
-78 °C to RT, 66% (3 steps)
Chemical structure
EtCOSt-Bu, i-Pr2NLi
THF
-110 °C, 85%

See the Aldol Addition
Chemical structure
  1. t-BuLi, (CH2NMe2)2
  2. AcOH
THF
-110 °C, 90%
Chemical structure
Na2CO3
MeOH
RT
Chemical structure
(PhOCH2CO)2O, DMAP
CH2Cl2, Pyr
0 °C
Chemical structure
MsCl
Pyr
0 °C
Chemical structure
LiOH, H2O2
THF, H2O
RT, 75% (4 steps)
Chemical structure
LiN3
HMPA, H2O
60 °C, 75%
Chemical structure
H2, PtO2
1 atm
THF
RT
Chemical structure
ClCO2(p-NO2Ph), NaHCO3
CH2Cl2, H2O
RT

See the Schotten-Baumann Reaction
Chemical structure
NH2OH.HCl, KH2PO4
MeOH, H2O
Reflux
Chemical structure
Et3N
CH2Cl2
RT, 70% (4 steps)
Chemical structure
Mesitaldehyde dimethyl acetal, CF3CO2H
CH2Cl2
0 °C, 85%
Chemical structure
EtSLi
HMPA
30 °C
Chemical structure + Chemical structure
Et3N
CH2Cl2
0 °C
Chemical structure
PhMe
110 °C, 70% (3 steps)

See the Corey-Nicolaou Macrolactonization
Chemical structure
p-PhBzCl, DMAP
CH2Cl2, Et3N
RT
Chemical structure
NaOH
THF, i-PrOH, H2O
RT, 70% (2 steps)
Chemical structure
SiO2, CF3CO2H
CH2Cl2, H2O
RT, 100%
Chemical structure + Chemical structure
AgOTf
CH2Cl2, PhMe
RT, 36%
Chemical structure + Chemical structure
Pb(ClO4)2
MeCN
RT
Chemical structure
H2O
MeOH
20% (2 steps)
Chemical structure
Na(Hg)
MeOH
75%
Chemical structure
NCS
Pyr
RT
Chemical structure
AgF
HMPA
70 °C
Chemical structure
H2O
5 °C, 40% (3 steps)
Chemical structure

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