Synthesis of Tetrodotoxin

Structure of Tetrodotoxin

C11H17N3O8

Principal investigatorJustin Du Bois
Publication year2003
Synthesis typeTotal
Number of steps 31 (linear)
References
J. Am. Chem. Soc. 2003, 125, 11510.
Part 1 of 1
intermediate structure
n-BuLi, i-Bu2AlH
Hexane(s), THF
intermediate structure + intermediate structure
NaOAc
THF
See the Aldol Addition
intermediate structure
Pyr, t-BuCOCl
THF
85% (3 steps)
intermediate structure
Pd/C, H2
THF
88%
intermediate structure
DMF, (COCl)2
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
80 atm
MeOH, CF3CO2H
intermediate structure
2,2-Dimethoxypropane, TsOH
THF
77% (2 steps)
intermediate structure
Et2NH
THF
83%
intermediate structure
n-Pr4N+ RuO4-, NMO
4 Å MS
CH2Cl2
94%
See the Ley-Griffith Oxidation
intermediate structure
PbCl2, CH2I2, Zn, TiCl4
THF
72%
See the Lombardo Methylenation
intermediate structure
(PhSe)2, PhIO, Pyr
PhCl
100 °C, 70%
intermediate structure
VinylMgBr, CuI
THF
See the Michael Addition
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
O3, NaBH4
CH2Cl2, MeOH
83%
intermediate structure
MsCl, Pyr
DCE
86%
intermediate structure
Rh2(CF3CONH)4, MgO, PhI(OAc)2
PhH
65 °C, 77%
intermediate structure
NaSePh
DMF, THF
77%
intermediate structure
Pyr, mCPBA
DCE
55 °C, 92%
intermediate structure
Boc2O, DMAP
Et3N, THF
intermediate structure
K2CO3
MeOH, THF
84% (2 steps)
intermediate structure
H2O
110 °C, 95%
intermediate structure + intermediate structure
HgCl2, Et3N
MeCN, MeOH
80%
intermediate structure
  1. O3
  2. Me2S
CH2Cl2, MeOH
intermediate structure
CF3CO2H
H2O
65% (2 steps)
intermediate structure
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