Synthesis of Saxitoxin

Structure of Saxitoxin

C10H17N7O4

Principal investigatorYoshito Kishi
Publication year1977
Synthesis typeTotal
Number of steps 19 (linear)
References
Part 1 of 1
intermediate structure
TsOH, HO(CH2)3OH
PhMe
Reflux
intermediate structure
NH2NH2
H2O, MeOH
Reflux, , 74% (2 steps)
intermediate structure
P2S5
PhH
intermediate structure + intermediate structure
NaHCO3
CH2Cl2
Reflux
intermediate structure
KOH
MeOH
50 °C, , 50% (3 steps)
intermediate structure + intermediate structure
Si(NCS)4
PhH
RT, , 75%
intermediate structure
NH2NH2
H2O, MeOH
RT
intermediate structure
NOCl
MeOH
-50 °C
intermediate structure
PhH
90 °C
intermediate structure
NH3
PhH
RT, , 75% (4 steps)
intermediate structure
BF3.OEt2, HS(CH2)3SH
MeCN
RT, , 63%
intermediate structure
(CF3CO)2O
AcOH
50 °C, 18 h, 50%
intermediate structure
NaHCO3, Et3O+ BF4-
CH2Cl2
RT
intermediate structure
EtCO2NH4
135 °C, , 33% (2 steps)
intermediate structure
BCl3
CH2Cl2
0 °C
intermediate structure
Ac2O
Pyr
RT, , 75% (2 steps)
intermediate structure
NBS
H2O, MeCN
15 °C
intermediate structure
MeOH
100 °C, , 30% (2 steps)
intermediate structure
ClSO2NCO
HCO2H
5 °C, , 50%
intermediate structure