Synthesis of Solandelactone E

Structure of Solandelactone E

C22H34O4

Principal investigatorVarinder K. Aggarwal
Publication year2010
Synthesis typeTotal
Number of steps 17 (3 parts)
References
Part 1 of 3
intermediate structure
AllylBr, In
THF
0 °C to RT, 4 h, 77%
intermediate structure
t-BuOOH, Ti(Oi-Pr)4, (-)-DET
CH2Cl2
-20 °C, 5 h, 75%
intermediate structure
DMAP, Et3N, PhSO2Cl
CH2Cl2
0 °C to RT, 60 min, 90%
intermediate structure
TMS2NNa, MeCN
THF
-78 to 0 °C, 3 h, 77%
"Also isolated was the C1-epimer (14 % yield)."
intermediate structure
3,4-Dihydropyran, Pyr.TsOH
CH2Cl2
RT, ON, 94%
intermediate structure
2,6-Lutidine, NaIO4, K2OsO2(OH)4
Dioxane , H2O
RT
intermediate structure + intermediate structure
TMS2NNa
THF
-78 °C to RT, ON, 59% (2 steps)
See the Wittig Reaction
"Aqueous HCl work-up cleaves the THP."
intermediate structure
Et3N
THF
0 °C to RT, 4 h
"Ar = 2,4,6-trichlorophenyl"
intermediate structure
DMAP
PhMe
60 to 90 °C, 34 h, 79% (2 steps)
"Ar = 2,4,6-trichlorophenyl"
intermediate structure
Ni (Raney), NaH2PO2
AcOH, H2O, Pyr
0 °C to RT, 4 h, 87%
intermediate structure
Part 2 of 3
intermediate structure + intermediate structure
NaH
THF
Reflux, 24 h, 85%
intermediate structure
  1. n-Bu3SnCl
  2. s-BuLi
Et2O
-78 °C to RT, ON, 42%
"The yield was 84 % brsm."
intermediate structure
HCl, NaIO4
H2O, MeOH
RT
intermediate structure + intermediate structure
TMS2NNa
THF
-78 °C to RT, ON, 80% (2 steps)
See the Wittig Reaction
intermediate structure
Part 3 of 3
intermediate structure + intermediate structure + intermediate structure
n-BuLi, (CH2NMe2)2
Et2O
-78 °C to RT, 2.5 h, 73%
intermediate structure
t-BuOOH, Ti(Oi-Pr)4
CH2Cl2
-10 °C, 5.5 h
intermediate structure
AcOH
MeOH
0 °C, ON, 68% (2 steps)
intermediate structure