Synthesis of Saxitoxin

Structure of Saxitoxin

C10H17N7O4

Principal investigator	Peter A. Jacobi
Publication year	1984
Synthesis type	Formal
Number of steps	16 (linear)
References	J. Am. Chem. Soc. 1984, 106, 5594. J. Am. Chem. Soc. 1981, 103, 239.

Part 1 of 1

intermediate structure

+

intermediate structure

SnCl4

MeNO2

60%

See the Friedel-Crafts Acylation

intermediate structure

HS(CH2)3SH, BF3.OEt2

74%

intermediate structure

KOH

H2O

80%

intermediate structure

(CF3CO)2O

PhH

92%

intermediate structure

BnNHNH2

THF

74%

intermediate structure

+

intermediate structure

BF3.OEt2

MeCN

Reflux, 8 h, 67%

intermediate structure

NaOMe, NaBH4

MeOH

RT, 5 h, 72%

intermediate structure

BH3.Me2S, BF3.OEt2

THF

Reflux, 2 h, 98%

intermediate structure

Pd

AcOH, HCO2H

RT, 60 min

intermediate structure

ClSO2NCO

Pyr, THF

0 °C, 2 h, 80% (2 steps)

intermediate structure

Na

NH3

-78 °C, 60 min, 75%

intermediate structure

Ac2O

Pyr

RT, 3 h, 73%

intermediate structure

Et3O+ BF4-, NaHCO3

CH2Cl2

RT, 2 h, 83%

intermediate structure

EtCO2NH4

135 °C, 30 min

intermediate structure

Ac2O

Pyr

RT, 8 h, 48% (2 steps)

intermediate structure

Report an error in this part

Remaining...

15% (3 steps)

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

intermediate structure