Synthesis of U-106305

Structure of U-106305

C28H41NO

Principal investigatorAndré B. Charette
Publication year1996
Synthesis typeTotal
Number of steps 18 (3 parts)
References
Part 1 of 3
intermediate structure
H2Cr2O7.2Pyr, Celite
CH2Cl2
RT, 2 h
intermediate structure
(EtO)2P(O)CH2CO2Et, NaH
THF
0 °C to RT, 12.5 h, 49% (2 steps)
intermediate structure
i-Bu2AlH
CH2Cl2
-78 to 0 °C, 3 h, 81%
intermediate structure
Et2Zn, CH2I2
DME, CH2Cl2
-20 °C to RT, 8.5 h, 90%
intermediate structure
H2Cr2O7.2Pyr, Celite
CH2Cl2
RT, 2 h
intermediate structure
(EtO)2P(O)CH2CO2Et, NaH
THF
0 °C to RT, 12.5 h, 41% (2 steps)
intermediate structure
i-Bu2AlH
CH2Cl2
-78 to 0 °C, 3 h, 99%
intermediate structure
Et2Zn, CH2I2
DME, CH2Cl2
-20 °C to RT, 8.5 h, 90%
intermediate structure
  1. NaH
  2. TIPSCl
DMF, THF
0 °C to RT, 8 h, 51%
intermediate structure
H2Cr2O7.2Pyr, Celite
CH2Cl2
RT, 2 h, 85%
intermediate structure
Part 2 of 3
intermediate structure
Et2Zn, CH2I2
DME, CH2Cl2
-20 °C to RT, 8.5 h
intermediate structure
MsCl, Et3N
CH2Cl2
0 °C, 30 min
intermediate structure + intermediate structure
NaH
DMF
0 °C to RT, 12 h
intermediate structure
mCPBA
CH2Cl2
RT, 3 h, 56% (4 steps)
intermediate structure
Part 3 of 3
intermediate structure + intermediate structure
TMS2NNa
DMF
-60 °C to RT, 90 min
intermediate structure
n-Bu4N+ F-
THF
RT, 2 h, 74% (2 steps)
"Also isolated was 18 % of the Z-isomer."
intermediate structure
H2Cr2O7.2Pyr, Celite
CH2Cl2
RT, 2 h, 87%
intermediate structure + intermediate structure
NaH
DME
0 °C to RT, 5 h, 80%
intermediate structure