Synthesis of Agelastatin A

Structure of Agelastatin A

C12H13BrN4O3

Principal investigatorNoritaka Chida
Publication year2009
Synthesis typeTotal
Number of steps 21 (linear)
References
Org. Lett. 2009, 11, 2687.
Part 1 of 1
intermediate structure
NaOH, TsCl, n-Bu4N+ HSO4-
CH2Cl2, H2O
RT, 2 h, 91%
intermediate structure
K2CO3, PhSH
DMF
RT, 12 h, 90%
intermediate structure
(COCl)2, DMSO, Et3N
CH2Cl2
-78 °C to RT, 80 min
See the Swern Oxidation
intermediate structure + intermediate structure
KOt-Bu
THF
0 °C, 30 min, 81% (2 steps)
See the Wittig Reaction
intermediate structure
AIBN, PhSH
PhH
85 °C, 90 min, 79%
intermediate structure
AcOH
H2O
40 °C, 24 h, 70%
"Recrystallized twice to afford pure E diene."
intermediate structure
DBU, Cl3CCN
CH2Cl2
-20 °C to RT, 20 min
intermediate structure
Na2CO3
o-Xylene
140 °C, 2.5 h, 58% (2 steps)
See the Overman Rearrangement
intermediate structure
mCPBA
CH2Cl2
-20 °C, 20 min, 97%
intermediate structure
P(OMe)3
MeOH
80 °C, 24 h
See the Evans-Mislow Rearrangement
intermediate structure
Grubbs catalyst (1st gen.)
CH2Cl2
RT, 15 min
See the Olefin Metathesis
intermediate structure
Pyr, Ms2O
CH2Cl2
0 °C to RT, 2.5 h, 58% (3 steps)
intermediate structure
i-Bu2AlH
CH2Cl2
-78 °C, 15 min
intermediate structure + intermediate structure
Et3N, HOBt, EDC
THF
RT, 12 h, 50% (2 steps)
intermediate structure
TsOH
H2O, Pyr
70 °C, 90 min, 81%
intermediate structure
3,4-Dihydropyran, Pyr.TsOH
CH2Cl2
RT, 3 h, 94%
intermediate structure + intermediate structure
Na2CO3
DMSO
100 °C, 90 min, 70%
intermediate structure
TsOH
MeOH
RT, 60 min, 90%
intermediate structure
IBX
DMSO
RT, 14 h, 98%
intermediate structure
Et3N
MeCN
-20 °C, 30 min
intermediate structure
(NH4)2Ce(NO3)6
H2O, MeCN
10 °C, 2 h, 54% (2 steps)
intermediate structure
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