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)