Synthesis of Saxitoxin

C10H17N7O4
Principal investigator | Peter A. Jacobi |
---|---|
Publication year | 1984 |
Synthesis type | Formal |
Number of steps | 16 (linear) |
References |
Part 1 of 1
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HS(CH2)3SH,
BF3.OEt2
74%

KOH
H2O
80%

(CF3CO)2O
PhH
92%

BnNHNH2
THF
74%


BF3.OEt2
MeCN
Reflux, 8 h, 67%

NaOMe,
NaBH4
MeOH
RT, 5 h, 72%

BH3.Me2S,
BF3.OEt2
THF
Reflux, 2 h, 98%

Pd
AcOH, HCO2H
RT, 60 min

ClSO2NCO
Pyr, THF
0 °C, 2 h, 80% (2 steps)

Na
NH3
-78 °C, 60 min, 75%

Ac2O
Pyr
RT, 3 h, 73%

Et3O+ BF4-,
NaHCO3
CH2Cl2
RT, 2 h, 83%

EtCO2NH4
135 °C, 30 min

Ac2O
Pyr
RT, 8 h, 48% (2 steps)

Remaining...
15% (3 steps)
"See: J. Am. Chem. Soc. 1977, 99, 2818."
