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
THF, H2O
intermediate structure
Me2NNH2, MgSO4
CH2Cl2
72% (2 steps)
intermediate structure
EtMgBr
THF
RT, 48 h
intermediate structure
CuSO4, Camphorsulfonic acid
Acetone
55% (2 steps)
intermediate structure
Li
NH3, Et2O
98%
See the Birch Reduction
intermediate structure
o-NO2PhSeCN, n-Bu3P
THF
intermediate structure
H2O2
THF, H2O
81% (2 steps)
intermediate structure
  1. O3
  2. NaHCO3
  3. Me2S
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
(CF3CO)2O, NaOAc, 2,6-Lutidine
Ac2O
RT, 60 min
intermediate structure
HgCl2, CaCO3
MeCN, H2O
RT, 2 h, 60% (2 steps)
intermediate structure
Part 2 of 3
intermediate structure
MeI, K2CO3
Acetone
intermediate structure
NaNH2, CO2
Et2O, NH3
intermediate structure
CDI
THF
intermediate structure
Me2SO4, K2CO3
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
TsCl, Et3N, DMAP
CH2Cl2
RT, 12 h, 82%
intermediate structure