Synthesis of Saxitoxin

Structure of Saxitoxin

C10H17N7O4

Principal investigatorJustin Du Bois
Publication year2006
Synthesis typeTotal
Number of steps 20 (linear)
References
Part 1 of 1
intermediate structure
HCO2H, ClSO2NCO
MeCN, DMA
0 °C to RT, 8 h, 75%
intermediate structure
PhI(OAc)2, MgO, Rh2(Ph3CCO2)4
CH2Cl2
RT, 1-4 h, 92%
intermediate structure + intermediate structure
BF3.OEt2, n-BuLi, ZnCl2
THF
-78 to 40 °C, 90 min, 70%
intermediate structure
H2, Lindlar Catalyst
THF
intermediate structure
NaN3, n-Bu4N+ I-
DMF
90% (2 steps)
intermediate structure
K2CO3, (4-MeOPh)CH2Cl, n-Bu4N+ I-
MeCN
85%
intermediate structure
Me3P
H2O, THF
intermediate structure
i-Pr2NEt, MeS(Cl)C=NSO2(p-MeOPh)
MeCN
72% (2 steps)
intermediate structure
DMAP, Pyr, Tf2O
CH2Cl2
intermediate structure
NaN3
DMF
-15 °C, , 70% (2 steps)
intermediate structure
(NH4)2Ce(NO3)6
CH2Cl2, t-BuOH
74%
intermediate structure
KOt-Bu, Cl2C=NSO2(p-MeOPh), TMS2NH
70%
"The yield was 88 % brsm."
intermediate structure
H2O
MeCN
70 °C, , 95%
intermediate structure
Me3P
H2O, THF
intermediate structure
AgNO3, Et3N
MeCN
65% (2 steps)
intermediate structure
Cl3CC(O)NCO
MeCN, THF
-78 °C
intermediate structure
K2CO3
MeOH
82% (2 steps)
intermediate structure
Na2CO3, OsCl3, Oxone
EtOAc, H2O, MeCN
57%
intermediate structure
(CF3CO)2O, B(CF3CO2)3
82%
intermediate structure
DCC, Pyr
DMSO, CF3CO2H
70%
intermediate structure