Synthesis of Ammosamide B

Structure of Ammosamide B

C12H10ClN5O2

Principal investigatorWilliam Fenical
Publication year2010
Synthesis typeTotal
Number of steps 17 (linear)
References
Part 1 of 1
intermediate structure
HNO3, H2SO4
H2O
0 °C, 90 min, 58%
intermediate structure
t-BuNH2
Dioxane
100 °C, ON, 87%
intermediate structure
MeI, NaH
DMF
0 °C to RT, 45 min
intermediate structure
CF3CO2H
CH2Cl2
RT, 30 min, 92% (2 steps)
intermediate structure + intermediate structure
CH2Cl2
3.5 h, 86%
See the Wittig Reaction
intermediate structure
CF3CO2H
100 °C, ON
intermediate structure
HNO3, H2SO4
H2O
RT, ON
intermediate structure
POCl3
100 °C, ON, 85% (3 steps)
intermediate structure
HI
MeCN, H2O
RT, ON
intermediate structure
(CF3CO)2O
Pyr
0 °C, 4 min, 74% (2 steps)
intermediate structure
CuCN
Pyr
80 °C, 2 h
intermediate structure
H2SO4
MeOH
60 °C, ON
intermediate structure
KOH
MeOH
50 °C, 4 h
intermediate structure
H2SO4
MeOH
60 °C, 60 min
intermediate structure
SOCl2
RT, 45 min
intermediate structure
(CF3CO)2O
Pyr
RT, 3 h, 8% (6 steps)
intermediate structure
Mg3N2
MeOH
0 to 80 °C, ON, 100%
intermediate structure