Synthesis of Saxitoxin

Structure of Saxitoxin

C10H17N7O4

Principal investigatorPeter A. Jacobi
Publication year1984
Synthesis typeFormal
Number of steps 16 (linear)
References
Part 1 of 1
intermediate structure + intermediate structure
SnCl4
MeNO2
60%
intermediate structure
HS(CH2)3SH, BF3.OEt2
74%
intermediate structure
KOH
H2O
80%
intermediate structure
(CF3CO)2O
PhH
92%
intermediate structure
BnNHNH2
THF
74%
intermediate structure + intermediate structure
BF3.OEt2
MeCN
Reflux, 8 h, 67%
intermediate structure
NaBH4, NaOMe
MeOH
RT, 5 h, 72%
intermediate structure
BH3.Me2S, BF3.OEt2
THF
Reflux, 2 h, 98%
intermediate structure
Pd
HCO2H, AcOH
RT, 60 min
intermediate structure
ClSO2NCO
THF, Pyr
0 °C, 2 h, 80% (2 steps)
intermediate structure
Na
NH3
-78 °C, 60 min, 75%
intermediate structure
Ac2O
Pyr
RT, 3 h, 73%
intermediate structure
Et3O+ BF4-, NaHCO3
CH2Cl2
RT, 2 h, 83%
intermediate structure
EtCO2NH4
135 °C, 30 min
intermediate structure
Ac2O
Pyr
RT, 8 h, 48% (2 steps)
intermediate structure
Remaining...
15% (3 steps)
"See: J. Am. Chem. Soc. 1977, 99, 2818."
intermediate structure