Synthesis of U-106305
C28H41NO
| Principal investigator | André B. Charette |
|---|---|
| Publication year | 1996 |
| Synthesis type | Total |
| Number of steps | 18 (3 parts) |
| References |
Part 1 of 3
H2Cr2O7.2Pyr,
Celite
4 Å MS
CH2Cl2
RT, 2 h
NaH,
(EtO)2P(O)CH2CO2Et
THF
0 °C to RT, 12.5 h, 49% (2 steps)
See the Horner-Wadsworth-Emmons Reaction
i-Bu2AlH
CH2Cl2
-78 to 0 °C, 3 h, 81%
Celite,
H2Cr2O7.2Pyr
4 Å MS
CH2Cl2
RT, 2 h
(EtO)2P(O)CH2CO2Et,
NaH
THF
0 °C to RT, 12.5 h, 41% (2 steps)
See the Horner-Wadsworth-Emmons Reaction
i-Bu2AlH
CH2Cl2
-78 to 0 °C, 3 h, 99%
- NaH
- TIPSCl
DMF, THF
0 °C to RT, 8 h, 51%
H2Cr2O7.2Pyr,
Celite
4 Å MS
CH2Cl2
RT, 2 h, 85%
Part 2 of 3
+
Et3N,
MsCl
CH2Cl2
0 °C, 30 min
+
NaH
DMF
0 °C to RT, 12 h
mCPBA
CH2Cl2
RT, 3 h, 56% (4 steps)
Part 3 of 3
+
+
+
n-Bu4N+ F-
THF
RT, 2 h, 74% (2 steps)
"Also isolated was 18 % of the Z-isomer."
H2Cr2O7.2Pyr,
Celite
4 Å MS
CH2Cl2
RT, 2 h, 87%
+