Synthesis of Asteltoxin
C23H30O7
Principal investigator | Stuart L. Schreiber |
---|---|
Publication year | 1984 |
Synthesis type | Total |
Number of steps | 20 (3 parts) |
References |
Part 1 of 3
+
+
HCl
H2O, THF
Me2NNH2,
MgSO4
CH2Cl2
72% (2 steps)
Camphorsulfonic acid,
CuSO4
Acetone
55% (2 steps)
o-NO2PhSeCN,
n-Bu3P
THF
- O3 , NaHCO3
- Me2S
CH2Cl2, MeOH
-78 °C to RT
n-BuLi
THF
-78 °C, 40 min, 67% (2 steps)
"Also isolated was the C1-epimer (21 % yield)."
Camphorsulfonic acid
CH2Cl2
RT, 8 h
CaCO3,
HgCl2
H2O, MeCN
RT, 2 h, 60% (2 steps)
Part 2 of 3
K2CO3,
MeI
Acetone
NaNH2,
CO2
Et2O, NH3
CDI
THF
K2CO3,
Me2SO4
Acetone
Part 3 of 3
+
DMAP,
Et3N,
TsCl
CH2Cl2
RT, 12 h, 82%