Synthesis of Saxitoxin

Structure of Saxitoxin

C10H17N7O4

Principal investigator	Justin Du Bois
Publication year	2006
Synthesis type	Total
Number of steps	20 (linear)
References	J. Am. Chem. Soc. 2006, 128, 3926. J. Am. Chem. Soc. 2003, 125, 2028.

Part 1 of 1

intermediate structure

HCO2H, ClSO2NCO

MeCN, DMA

0 °C to RT, 8 h, 75%

intermediate structure

PhI(OAc)2, MgO, Rh2(Ph3CCO2)4

CH2Cl2

RT, 1-4 h, 92%

intermediate structure

+

intermediate structure

BF3.OEt2, n-BuLi, ZnCl2

THF

-78 to 40 °C, 90 min, 70%

intermediate structure

H2, Lindlar Catalyst

THF

intermediate structure

NaN3, n-Bu4N+ I-

DMF

90% (2 steps)

intermediate structure

K2CO3, (4-MeOPh)CH2Cl, n-Bu4N+ I-

MeCN

85%

intermediate structure

Me3P

H2O, THF

See the Staudinger Reaction

intermediate structure

i-Pr2NEt, MeS(Cl)C=NSO2(p-MeOPh)

MeCN

72% (2 steps)

intermediate structure

Tf2O, Pyr, DMAP

CH2Cl2

intermediate structure

NaN3

DMF

-15 °C, 70% (2 steps)

intermediate structure

(NH4)2Ce(NO3)6

CH2Cl2, t-BuOH

74%

intermediate structure

KOt-Bu, Cl2C=NSO2(p-MeOPh), TMS2NH

70%

"The yield was 88 % brsm."

intermediate structure

H2O

MeCN

70 °C, 95%

intermediate structure

Me3P

H2O, THF

See the Staudinger Reaction

intermediate structure

AgNO3, Et3N

MeCN

65% (2 steps)

intermediate structure

Cl3CC(O)NCO

MeCN, THF

-78 °C

intermediate structure

K2CO3

MeOH

82% (2 steps)

intermediate structure

Na2CO3, OsCl3, Oxone

EtOAc, H2O, MeCN

57%

intermediate structure

(CF3CO)2O, B(CF3CO2)3

82%

intermediate structure

DCC, Pyr

DMSO, CF3CO2H

70%

See the Pfitzner-Moffatt oxidation

intermediate structure

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