Submitted by Nicolas Millius
A unified strategy for the synthesis of the C1-C14 fragment of marinolic
acids, mupirocins, pseudomonic acids and thiomarinols: total synthesis
of pseudomonic acid methyl monate C
Problem:
OH
OTBS
O
NBS, NaOAc.3H2O
NaHCO3, THF/2H2O
0 ºC, 5 min, 95%
O
HO
1
OTBS
O
2
OH
trimethyl orthoacetate
propionic acid, 140 ºC
16 h, 90%
OTBS
MeO2C
O
OTBS
O
4
3
OH
HO
CO2Me
O
OH
Pseudomonic acid methyl monate C
•
•
Give the mechanism from 1 to 2. What is the name of this reaction?
Give the mechanism from 3 to 4. What is the name of this reaction?
Submitted by Nicolas Millius
Solution:
•
1 to 2: Achmatowicz reaction
OH
O
Br
R
1
OH
O+
Br
OH
HO
O
R
R
Br
H
O
H2O
N
O
R
R
O
O
HO
O
O
HO
2
•
3 to 4: Johnson-Claisen rearrangement
Me
MeO
OH
OMe
OMe
OMe
Me
OMe
OMe
Me
OMe
O
+
O
R
O
R
3
MeOH
OMe
MeO2C
O
O
O
R
O
R
OMe
O
R
4
Comments:
The Achmatowicz reaction is working also with a peroxide instead of NBS.
References:
Y. Sridhar, P. Srihari, Org. Biomol. Chem. 2014, 12, 2950 – 2959.
Submitted by Nicolas Millius
Keywords:
Achmatovicz reaction, Johnson-Claisen rearrangement

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