Synthesis of Agelastatin A

C12H13BrN4O3
Principal investigator | Noritaka Chida |
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Publication year | 2009 |
Synthesis type | Total |
Number of steps | 21 (linear) |
References |
Part 1 of 1
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NaOH,
TsCl,
n-Bu4N+ HSO4-
CH2Cl2, H2O
RT, 2 h, 91%

K2CO3,
PhSH
DMF
RT, 12 h, 90%




AIBN,
PhSH
PhH
85 °C, 90 min, 79%

AcOH
H2O
40 °C, 24 h, 70%
"Recrystallized twice to afford pure E diene."

DBU,
Cl3CCN
CH2Cl2
-20 °C to RT, 20 min


mCPBA
CH2Cl2
-20 °C, 20 min, 97%



Pyr,
Ms2O
CH2Cl2
0 °C to RT, 2.5 h, 58% (3 steps)

i-Bu2AlH
CH2Cl2
-78 °C, 15 min


Et3N,
HOBt,
EDC
THF
RT, 12 h, 50% (2 steps)

TsOH
H2O, Pyr
70 °C, 90 min, 81%

3,4-Dihydropyran,
Pyr.TsOH
CH2Cl2
RT, 3 h, 94%


Na2CO3
DMSO
100 °C, 90 min, 70%

TsOH
MeOH
RT, 60 min, 90%

IBX
DMSO
RT, 14 h, 98%

Et3N
MeCN
-20 °C, 30 min

(NH4)2Ce(NO3)6
H2O, MeCN
10 °C, 2 h, 54% (2 steps)
