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Named reactions

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Search synthesis

Saxitoxin

Chemical structure of Saxitoxin
C10H17N7O4
Author Justin Du Bois
Publication year 2006
Synthesis type Total synthesis
Number of steps 20 (linear)
References

Browse hundreds of other total syntheses.

Part 1 of 1
Chemical structure
ClSO2NCO, HCO2H
MeCN, DMA
0 °C to RT, 8 h, 75%
Chemical structure
Rh2(Ph3CCO2)4, PhI(OAc)2, MgO
CH2Cl2
RT, 1-4 h, 92%
Chemical structure + Chemical structure
n-BuLi, ZnCl2, BF3.OEt2
THF
-78 to 40 °C, 90 min, 70%
Chemical structure
H2, Lindlar Catalyst
THF
Chemical structure
NaN3, n-Bu4N+ I-
DMF
90% (2 steps)
Chemical structure
(4-MeOPh)CH2Cl, n-Bu4N+ I-, K2CO3
MeCN
85%
Chemical structure
Me3P
THF, H2O

See the Staudinger Reaction
Chemical structure
MeS(Cl)C=NSO2(p-MeOPh), i-Pr2NEt
MeCN
72% (2 steps)
Chemical structure
Tf2O, Pyr, DMAP
CH2Cl2
Chemical structure
NaN3
DMF
-15 °C, 70% (2 steps)
Chemical structure
(NH4)2Ce(NO3)6
t-BuOH, CH2Cl2
74%
Chemical structure
Cl2C=NSO2(p-MeOPh), KOt-Bu, TMS2NH
70%

The yield was 88 % brsm.
Chemical structure
H2O
MeCN
70 °C, 95%
Chemical structure
Me3P
THF, H2O

See the Staudinger Reaction
Chemical structure
AgNO3, Et3N
MeCN
65% (2 steps)
Chemical structure
Cl3CC(O)NCO
THF, MeCN
-78 °C
Chemical structure
K2CO3
MeOH
82% (2 steps)
Chemical structure
OsCl3, Oxone ®, Na2CO3
EtOAc, MeCN, H2O
57%
Chemical structure
B(CF3CO2)3, (CF3CO)2O
82%
Chemical structure
DCC, Pyr
CF3CO2H, DMSO
70%

See the Pfitzner-Moffatt oxidation
Chemical structure

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