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Named reactions

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Search synthesis

Tetrodotoxin

"To our friend and colleague Harry S. Mosher (1915-2001) for his inspiration and in tribute to his work on tetrodotoxin."

Chemical structure of Tetrodotoxin
C11H17N3O8
Author Justin Du Bois
Publication year 2003
Synthesis type Total synthesis
Number of steps 31 (linear)
Reference

Browse hundreds of other total syntheses.

Part 1 of 1
Chemical structure
i-Bu2AlH, n-BuLi
THF, Hexane(s)
Chemical structure + Chemical structure
NaOAc
THF

See the Aldol Addition
Chemical structure
t-BuCOCl, Pyr
THF
85% (3 steps)
Chemical structure
H2, Pd/C
THF
88%
Chemical structure
(COCl)2, DMF
THF
Chemical structure
CH2N2
CH2Cl2
63-70% (2 steps)
Chemical structure
Rh2(TrCONH)4
CCl4
Chemical structure
BH3.NH3
CH2Cl2, MeOH
75% (2 steps)
Chemical structure
H2, Rh/C
80 atm
CF3CO2H, MeOH
Chemical structure
TsOH, 2,2-Dimethoxypropane
THF
77% (2 steps)
Chemical structure
Et2NH
THF
83%
Chemical structure
n-Pr4N+ RuO4-, NMO
4 Å MS
CH2Cl2
94%

See the Ley-Griffith Oxidation
Chemical structure
Zn, TiCl4, CH2I2, PbCl2
THF
72%

See the Lombardo Methylenation
Chemical structure
(PhSe)2, PhIO, Pyr
PhCl
100 °C, 70%
Chemical structure
VinylMgBr, CuI
THF

See the Michael Addition
Chemical structure
BH3.NH2t-Bu
DCE
77% (2 steps)
Chemical structure
t-BuCO2H
PhCl
200 °C
Chemical structure
NaOMe
THF, MeOH
78% (2 steps)
Chemical structure
Cl3CC(O)NCO
CH2Cl2
Chemical structure
Zn
MeOH
93% (2 steps)
Chemical structure
O3, NaBH4
CH2Cl2, MeOH
83%
Chemical structure
MsCl, Pyr
DCE
86%
Chemical structure
Rh2(CF3CONH)4, PhI(OAc)2, MgO
PhH
65 °C, 77%
Chemical structure
NaSePh
THF, DMF
77%
Chemical structure
mCPBA, Pyr
DCE
55 °C, 92%
Chemical structure
Boc2O, DMAP
THF, Et3N
Chemical structure
K2CO3
THF, MeOH
84% (2 steps)
Chemical structure
H2O
110 °C, 95%
Chemical structure + Chemical structure
HgCl2, Et3N
MeCN, MeOH
80%
Chemical structure
  1. O3
  2. Me2S
CH2Cl2, MeOH
Chemical structure
CF3CO2H
H2O
65% (2 steps)
Chemical structure

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