Synthesis of Elailoide
C42H68O12
| Principal investigator | David A. Evans |
|---|---|
| Publication year | 1997 |
| Synthesis type | Total |
| Number of steps | 22 (2 parts) |
| References |
Part 1 of 2
+
EtI,
i-Pr2NLi
THF
-78 to 20 °C, 24 h, 82%
TBSOTf,
2,6-Lutidine
CH2Cl2
60 min, 0 °C, 98%
i-Bu2AlH
CH2Cl2
-78 to -40 °C, 90 min, 100%
+
BF3.OEt2
CH2Cl2
-78 °C, 45 min, 89%
n-Bu4N+ F-
THF
RT, 10 min, 96%
t-Bu2Si(OTf)2,
2,6-Lutidine
CH2Cl2
0 °C, 60 min, 91%
- O3
- Me2S
CH2Cl2, MeOH
-78 °C to RT, 3 h, 90%
Part 2 of 2
+
+
+
+
2,6-Lutidine,
TESOTf
CH2Cl2
0 °C, 30 min, 92%
LiBH4
Et2O, H2O
RT, 3 h, 87%
DMAP,
Et3N,
Ph3CCl
CH2Cl2
RT, 6 h, 92%
- 9-BBN
- H2O , H2O2
THF
0 °C, 3 h, 89%
+
Pyr.HF
THF
0 °C, 4 h, 93%
KOH
H2O, MeOH, THF
RT, 98%
Camphorsulfonic acid
MeOH, THF
RT, 65%
+
Pyr,
Pyr.HF
H2O, THF
RT, 3 h, 91%