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Named reactions

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Search synthesis

Saxitoxin

"Dedicated to Professor Max Tishler and Elizabeth Tishler on the occasion of their 50th wedding anniversary."

Chemical structure of Saxitoxin
C10H17N7O4
Author Peter A. Jacobi
Publication year 1984
Synthesis type Formal synthesis
Number of steps 18 (linear)
References

Browse hundreds of other total syntheses.

Part 1 of 1
Chemical structure
+
Chemical structure
SnCl4
MeNO2
60%

See the Friedel-Crafts Acylation
Chemical structure
HS(CH2)3SH, BF3.OEt2
74%
Chemical structure
KOH
H2O
80%
Chemical structure
(CF3CO)2O
PhH
92%
Chemical structure
BnNHNH2
THF
74%
Chemical structure + Chemical structure
BF3.OEt2
MeCN
Reflux, 8 h, 67%
Chemical structure
NaBH4, NaOMe
MeOH
RT, 5 h, 72%
Chemical structure
BH3.Me2S, BF3.OEt2
THF
Reflux, 2 h, 98%
Chemical structure
Pd
HCO2H, AcOH
RT, 60 min
Chemical structure
ClSO2NCO
THF, Pyr
0 °C, 2 h, 80% (2 steps)
Chemical structure
Na
NH3
-78 °C, 60 min, 75%
Chemical structure
Ac2O
Pyr
RT, 3 h, 73%
Chemical structure
Et3O+ BF4-, NaHCO3
CH2Cl2
RT, 2 h, 83%
Chemical structure
EtCO2NH4
135 °C, 30 min
Chemical structure
Ac2O
Pyr
RT, 8 h, 48% (2 steps)
Chemical structure

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Remaining...
15% (3 steps)

See: J. Am. Chem. Soc. 1977, 99, 2818.
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