Synthesis of Saxitoxin

C10H17N7O4
Principal investigator | Yoshito Kishi |
---|---|
Publication year | 1977 |
Synthesis type | Total |
Number of steps | 19 (linear) |
References |
Part 1 of 1
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TsOH,
HO(CH2)3OH
PhMe
Reflux

NH2NH2
H2O, MeOH
Reflux, 74% (2 steps)

P2S5
PhH



KOH
MeOH
50 °C, 50% (3 steps)



NH2NH2
H2O, MeOH
RT

NOCl
MeOH
-50 °C


NH3
PhH
RT, 75% (4 steps)

HS(CH2)3SH,
BF3.OEt2
MeCN
RT, 63%

(CF3CO)2O
AcOH
50 °C, 18 h, 50%

NaHCO3,
Et3O+ BF4-
CH2Cl2
RT

EtCO2NH4
135 °C, 33% (2 steps)

BCl3
CH2Cl2
0 °C

Ac2O
Pyr
RT, 75% (2 steps)

NBS
H2O, MeCN
15 °C

MeOH
100 °C, 30% (2 steps)

ClSO2NCO
HCO2H
5 °C, 50%
