Synthesis of Asteltoxin

Structure of Asteltoxin

C23H30O7

Principal investigatorStuart L. Schreiber
Publication year1984
Synthesis typeTotal
Number of steps 20 (3 parts)
References
Part 1 of 3
intermediate structure + intermediate structure
PhH
RT, 6 h, 63%
intermediate structure
mCPBA, NaHCO3
CH2Cl2
80%
intermediate structure
HCl
H2O, THF
intermediate structure
Me2NNH2, MgSO4
CH2Cl2
72% (2 steps)
intermediate structure
EtMgBr
THF
RT, 48 h
intermediate structure
Camphorsulfonic acid, CuSO4
Acetone
55% (2 steps)
intermediate structure
Li
Et2O, NH3
98%
See the Birch Reduction
intermediate structure
n-Bu3P, o-NO2PhSeCN
THF
intermediate structure
H2O2
H2O, THF
81% (2 steps)
intermediate structure
  1. Me2S
  2. NaHCO3
  3. O3
CH2Cl2, MeOH
-78 °C to RT
intermediate structure + intermediate structure
n-BuLi
THF
-78 °C, 40 min, 67% (2 steps)
"Also isolated was the C1-epimer (21 % yield)."
intermediate structure
Camphorsulfonic acid
CH2Cl2
RT, 8 h
intermediate structure
2,6-Lutidine, NaOAc, (CF3CO)2O
Ac2O
RT, 60 min
intermediate structure
CaCO3, HgCl2
H2O, MeCN
RT, 2 h, 60% (2 steps)
intermediate structure
Part 2 of 3
intermediate structure
K2CO3, MeI
Acetone
intermediate structure
NaNH2, CO2
Et2O, NH3
intermediate structure
CDI
THF
intermediate structure
K2CO3, Me2SO4
Acetone
intermediate structure
Part 3 of 3
intermediate structure + intermediate structure
i-Pr2NLi, HMPA
THF
-78 °C, 20 min, 80%
See the Aldol Addition
intermediate structure
DMAP, Et3N, TsCl
CH2Cl2
RT, 12 h, 82%
intermediate structure