Synthesis of Asteltoxin

C23H30O7
Principal investigator | Stuart L. Schreiber |
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Publication year | 1984 |
Synthesis type | Total |
Number of steps | 20 (3 parts) |
References |
Part 1 of 3
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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
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DMAP,
Et3N,
TsCl
CH2Cl2
RT, 12 h, 82%
