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%


