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Named reactions

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Agelastatin A

Chemical structure of Agelastatin_A
C12H13BrN4O3
Author Noritaka Chida
Publication year 2009
Synthesis type Total synthesis
Number of steps 21 (linear)
Reference

Browse hundreds of other total syntheses.

Part 1 of 1
Chemical structure
TsCl, NaOH, n-Bu4N+ HSO4-
CH2Cl2, H2O
RT, 2 h, 91 %
Chemical structure
PhSH, K2CO3
DMF
RT, 12 h, 90 %
Chemical structure
(COCl)2, DMSO, Et3N
CH2Cl2
-78 °C to RT, 80 min

See the Swern Oxidation
Chemical structure
+
Chemical structure
KOt-Bu
THF
0 °C, 30 min, 81 % (2 steps)

Selectivity : 83:17 Z/E
See the Wittig Reaction
Chemical structure
AIBN, PhSH
PhH
85 °C, 90 min, 79 %

Selectivity : 91:09 E/Z
Chemical structure
AcOH
H2O
40 °C, 24 h, 70 %

Recrystallized twice to afford pure E diene.
Chemical structure
Cl3CCN, DBU
CH2Cl2
-20 °C to RT, 20 min
Chemical structure
Na2CO3
o-Xylene
140 °C, 2.5 h, 58 % (2 steps)

See the Overman Rearrangement
Chemical structure
mCPBA
CH2Cl2
-20 °C, 20 min, 97 %
Chemical structure
P(OMe)3
MeOH
80 °C, 24 h

See the Evans-Mislow Rearrangement
Chemical structure
Grubbs catalyst (1st gen.)
CH2Cl2
RT, 15 min

See the Olefin Metathesis
Chemical structure
Ms2O, Pyr
CH2Cl2
0 °C to RT, 2.5 h, 58 % (3 steps)
Chemical structure
i-Bu2AlH
CH2Cl2
-78 °C, 15 min
Chemical structure
+
Chemical structure
EDC, HOBt, Et3N
THF
RT, 12 h, 50 % (2 steps)
Chemical structure
TsOH
Pyr, H2O
70 °C, 90 min, 81 %
Chemical structure
3,4-Dihydropyran, Pyr.TsOH
CH2Cl2
RT, 3 h, 94 %
Chemical structure
+
Chemical structure
Na2CO3
DMSO
100 °C, 90 min, 70 %
Chemical structure
TsOH
MeOH
RT, 60 min, 90 %
Chemical structure
IBX
DMSO
RT, 14 h, 98 %
Chemical structure
Et3N
MeCN
-20 °C, 30 min
Chemical structure
(NH4)2Ce(NO3)6
MeCN, H2O
10 °C, 2 h, 54 % (2 steps)
Chemical structure

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