Synthesis of Tetrodotoxin

C11H17N3O8
Principal investigator | Justin Du Bois |
---|---|
Publication year | 2003 |
Synthesis type | Total |
Number of steps | 31 (linear) |
References |
Part 1 of 1
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n-BuLi,
i-Bu2AlH
Hexane(s), THF



Pyr,
t-BuCOCl
THF
85% (3 steps)

Pd/C,
H2
THF
88%

DMF,
(COCl)2
THF

CH2N2
CH2Cl2
63-70% (2 steps)

Rh2(TrCONH)4
CCl4

BH3.NH3
CH2Cl2, MeOH
75% (2 steps)

H2,
Rh/C
80 atm
MeOH, CF3CO2H

2,2-Dimethoxypropane,
TsOH
THF
77% (2 steps)

Et2NH
THF
83%



(PhSe)2,
PhIO,
Pyr
PhCl
100 °C, 70%


BH3.NH2t-Bu
DCE
77% (2 steps)

t-BuCO2H
PhCl
200 °C

NaOMe
MeOH, THF
78% (2 steps)

Cl3CC(O)NCO
CH2Cl2

Zn
MeOH
93% (2 steps)

O3,
NaBH4
CH2Cl2, MeOH
83%

MsCl,
Pyr
DCE
86%

Rh2(CF3CONH)4,
MgO,
PhI(OAc)2
PhH
65 °C, 77%

NaSePh
DMF, THF
77%

Pyr,
mCPBA
DCE
55 °C, 92%

Boc2O,
DMAP
Et3N, THF

K2CO3
MeOH, THF
84% (2 steps)

H2O
110 °C, 95%


HgCl2,
Et3N
MeCN, MeOH
80%

- O3
- Me2S
CH2Cl2, MeOH

CF3CO2H
H2O
65% (2 steps)
