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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	J. Am. Chem. Soc. 1981, 103, 3210. J. Am. Chem. Soc. 1981, 103, 3213. J. Am. Chem. Soc. 1981, 103, 3215.

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Part 1 of 4

Chemical structure

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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

MeOCH₂I, KH

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

o-NO₂PhSeCN, n-Bu₃P, H₂O₂

THF, H₂O
RT

See the Grieco Dehydration

Chemical structure

O₃, Me₂S

CH₂Cl₂, MeOH
-78 °C to RT, 80 % (3 steps)

Chemical structure

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Part 4 of 4

Chemical structure

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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

KH, 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

o-NO₂PhSeCN, n-Bu₃P, H₂O₂

THF, H₂O
RT

See the Grieco Dehydration

Chemical structure

O₃, 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

t-BuLi, (CH₂NMe₂)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

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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

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Chemical structure

AgOTf

CH₂Cl₂, PhMe
RT, 36 %

Chemical structure

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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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