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
+
+
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."