Synthesis of Tetrodotoxin

Structure of Tetrodotoxin

C11H17N3O8

Principal investigatorJustin Du Bois
Publication year2003
Synthesis typeTotal
Number of steps 31 (linear)
References
Part 1 of 1
intermediate structure
i-Bu2AlH, n-BuLi
Hexane(s), THF
intermediate structure + intermediate structure
NaOAc
THF
See the Aldol Addition
intermediate structure
t-BuCOCl, Pyr
THF
85% (3 steps)
intermediate structure
H2, Pd/C
THF
88%
intermediate structure
(COCl)2, DMF
THF
intermediate structure
CH2N2
CH2Cl2
63-70% (2 steps)
intermediate structure
Rh2(TrCONH)4
CCl4
intermediate structure
BH3.NH3
CH2Cl2, MeOH
75% (2 steps)
intermediate structure
H2, Rh/C
MeOH, CF3CO2H
intermediate structure
TsOH, 2,2-Dimethoxypropane
THF
77% (2 steps)
intermediate structure
Et2NH
THF
83%
intermediate structure
NMO, n-Pr4N+ RuO4-
CH2Cl2
94%
intermediate structure
TiCl4, Zn, CH2I2, PbCl2
THF
72%
intermediate structure
Pyr, PhIO, (PhSe)2
PhCl
100 °C, , 70%
intermediate structure
CuI, VinylMgBr
THF
intermediate structure
BH3.NH2t-Bu
DCE
77% (2 steps)
intermediate structure
t-BuCO2H
PhCl
200 °C
intermediate structure
NaOMe
MeOH, THF
78% (2 steps)
intermediate structure
Cl3CC(O)NCO
CH2Cl2
intermediate structure
Zn
MeOH
93% (2 steps)
intermediate structure
NaBH4, O3
CH2Cl2, MeOH
83%
intermediate structure
MsCl, Pyr
DCE
86%
intermediate structure
Rh2(CF3CONH)4, PhI(OAc)2, MgO
PhH
65 °C, , 77%
intermediate structure
NaSePh
DMF, THF
77%
intermediate structure
mCPBA, Pyr
DCE
55 °C, , 92%
intermediate structure
DMAP, Boc2O
Et3N, THF
intermediate structure
K2CO3
MeOH, THF
84% (2 steps)
intermediate structure
H2O
110 °C, , 95%
intermediate structure + intermediate structure
Et3N, HgCl2
MeCN, MeOH
80%
intermediate structure
  1. Me2S
  2. O3
CH2Cl2, MeOH
intermediate structure
CF3CO2H
H2O
65% (2 steps)
intermediate structure