Synthesis of Solandelactone E
C22H34O4
| Principal investigator | Varinder K. Aggarwal |
|---|---|
| Publication year | 2010 |
| Synthesis type | Total |
| Number of steps | 17 (3 parts) |
| References |
Part 1 of 3
+
AllylBr,
In
THF
0 °C to RT, 4 h, 77%
DMAP,
Et3N,
PhSO2Cl
CH2Cl2
0 °C to RT, 60 min, 90%
MeCN,
TMS2NNa
THF
-78 to 0 °C, 3 h, 77%
"Also isolated was the C1-epimer (14 % yield)."
Pyr.TsOH,
3,4-Dihydropyran
CH2Cl2
RT, ON, 94%
+
TMS2NNa
THF
-78 °C to RT, ON, 59% (2 steps)
See the Wittig Reaction
"Aqueous HCl work-up cleaves the THP."
Et3N
THF
0 °C to RT, 4 h
"Ar = 2,4,6-trichlorophenyl"
DMAP
PhMe
60 to 90 °C, 34 h, 79% (2 steps)
See the Yamaguchi Esterification
"Ar = 2,4,6-trichlorophenyl"
Ni (Raney),
NaH2PO2
AcOH, H2O, Pyr
0 °C to RT, 4 h, 87%
Part 2 of 3
+
+
+
NaH
THF
Reflux, 24 h, 85%
- s-BuLi
- n-Bu3SnCl
Et2O
-78 °C to RT, ON, 42%
"The yield was 84 % brsm."
HCl,
NaIO4
H2O, MeOH
RT
+
Part 3 of 3
+
+
+
+
n-BuLi,
(CH2NMe2)2
Et2O
-78 °C to RT, 2.5 h, 73%
t-BuOOH,
Ti(Oi-Pr)4
CH2Cl2
-10 °C, 5.5 h
AcOH
MeOH
0 °C, ON, 68% (2 steps)