Synthesis of Saxitoxin

C10H17N7O4
Principal investigator | Justin Du Bois |
---|---|
Publication year | 2006 |
Synthesis type | Total |
Number of steps | 20 (linear) |
References |
Part 1 of 1
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HCO2H,
ClSO2NCO
MeCN, DMA
0 °C to RT, 8 h, 75%

PhI(OAc)2,
MgO,
Rh2(Ph3CCO2)4
CH2Cl2
RT, 1-4 h, 92%


BF3.OEt2,
n-BuLi,
ZnCl2
THF
-78 to 40 °C, 90 min, 70%

H2,
Lindlar Catalyst
THF

NaN3,
n-Bu4N+ I-
DMF
90% (2 steps)

K2CO3,
(4-MeOPh)CH2Cl,
n-Bu4N+ I-
MeCN
85%


i-Pr2NEt,
MeS(Cl)C=NSO2(p-MeOPh)
MeCN
72% (2 steps)

Tf2O,
Pyr,
DMAP
CH2Cl2

NaN3
DMF
-15 °C, 70% (2 steps)

(NH4)2Ce(NO3)6
CH2Cl2, t-BuOH
74%

KOt-Bu,
Cl2C=NSO2(p-MeOPh),
TMS2NH
70%
"The yield was 88 % brsm."

H2O
MeCN
70 °C, 95%


AgNO3,
Et3N
MeCN
65% (2 steps)

Cl3CC(O)NCO
MeCN, THF
-78 °C

K2CO3
MeOH
82% (2 steps)

Na2CO3,
OsCl3,
Oxone
EtOAc, H2O, MeCN
57%

(CF3CO)2O,
B(CF3CO2)3
82%

