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Cylindrospermopsin
| Author | Barry B. Snider |
|---|---|
| Publication year | 2000 |
| Synthesis type | Total synthesis |
| Number of steps | 24 (3 parts) |
| Reference |
Browse hundreds of other total syntheses.
Part 1 of 3
PCl5, POCl3
Reflux, 2 d
0 °C to RT, 12 h, 57 % (2 steps)
LiBH4
THF, EtOH
RT, 2 h, 93 %
RT, 2 h, 93 %
Part 2 of 3
+ 
ClCO2CH2CCl3
THF
-30 °C, 2.5 h, 49 %
The yield was 87 % brsm.
-30 °C, 2.5 h, 49 %
The yield was 87 % brsm.
Zn
CH2Cl2, AcOH
RT, 5 h, 96 %
RT, 5 h, 96 %
Li(s-Bu)3BH
THF
-78 °C, 2 h, 94 %
-78 °C, 2 h, 94 %
ClCO2Bn, Na2CO3
THF
RT, ON, 96 %
RT, ON, 96 %
TBSCl, Imidazole, DMAP
CH2Cl2
RT, ON, 89 %
RT, ON, 89 %
Part 3 of 3
+ 
TBSCl, Imidazole
CH2Cl2
RT, 5 h, 88 %
RT, 5 h, 88 %
O3, Me2S
CH2Cl2
-78 °C, 20 min, 72 %
-78 °C, 20 min, 72 %
BnNH2, NaBH3CN, Na2SO4
PhMe, MeOH, AcOH
RT, 4 h, 68 %
RT, 4 h, 68 %
H2, Pd/C
1 atm
MeOH
RT, ON
1 atm
RT, ON
BrCN
PhMe
RT, 5 h
RT, 5 h
NaH, ClCO2Bn
THF
0 °C to RT, 8 h, 45 % (3 steps)
0 °C to RT, 8 h, 45 % (3 steps)
n-Bu4N+ F-
THF
RT, ON, 83 %
RT, ON, 83 %
MnO2
CH2Cl2
RT, 60 min, 87 %
RT, 60 min, 87 %
Ac2O
Pyr
RT, ON, 87 %
Selectivity : 83 : 17
RT, ON, 87 %
Selectivity : 83 : 17
+ 
CuBr2
EtOAc
35 °C, 20 min
35 °C, 20 min
H2, Pd(OH)2/C
1 atm
MeOH
RT, 8 h, 42 % (2 steps)
Also isolated was the C7-epimer (28 % yield).
1 atm
RT, 8 h, 42 % (2 steps)
Also isolated was the C7-epimer (28 % yield).
HCl
H2O
100 °C, 6 h, 95 %
100 °C, 6 h, 95 %
SO3.DMF, Na2SO4
Pyr
RT, ON, 50-70 %
RT, ON, 50-70 %
