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Named reactions

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Search synthesis

U-106305

Chemical structure of U-106305
C28H41NO
Author André B. Charette
Publication year 1996
Synthesis type Total synthesis
Number of steps 18 (3 parts)
Reference

Browse hundreds of other total syntheses.

Part 1 of 3
Chemical structure
H2Cr2O7.2Pyr, Celite ®
4 Å MS
CH2Cl2
RT, 2 h
Chemical structure
(EtO)2P(O)CH2CO2Et, NaH
THF
0 °C to RT, 12.5 h, 49% (2 steps)

See the Horner-Wadsworth-Emmons Reaction
Chemical structure
i-Bu2AlH
CH2Cl2
-78 to 0 °C, 3 h, 81%
Chemical structure
Reagent structure
Et2Zn, CH2I2
DME, CH2Cl2
-20 °C to RT, 8.5 h, 90%

See the Charette Asymmetric Cyclopropanation
Chemical structure
H2Cr2O7.2Pyr, Celite ®
4 Å MS
CH2Cl2
RT, 2 h
Chemical structure
(EtO)2P(O)CH2CO2Et, NaH
THF
0 °C to RT, 12.5 h, 41% (2 steps)

See the Horner-Wadsworth-Emmons Reaction
Chemical structure
i-Bu2AlH
CH2Cl2
-78 to 0 °C, 3 h, 99%
Chemical structure
Reagent structure
Et2Zn, CH2I2
DME, CH2Cl2
-20 °C to RT, 8.5 h, 90%

See the Charette Asymmetric Cyclopropanation
Chemical structure
  1. NaH
  2. TIPSCl
DMF, THF
0 °C to RT, 8 h, 51%
Chemical structure
H2Cr2O7.2Pyr, Celite ®
4 Å MS
CH2Cl2
RT, 2 h, 85%
Chemical structure

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Part 2 of 3
Chemical structure
Reagent structure
Et2Zn, CH2I2
DME, CH2Cl2
-20 °C to RT, 8.5 h

Selectivity : 96:04 er
See the Charette Asymmetric Cyclopropanation
Chemical structure
MsCl, Et3N
CH2Cl2
0 °C, 30 min
Chemical structure + Chemical structure
NaH
DMF
0 °C to RT, 12 h
Chemical structure
mCPBA
CH2Cl2
RT, 3 h, 56% (4 steps)
Chemical structure

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Part 3 of 3
Chemical structure
+
Chemical structure
TMS2NNa
DMF
-60 °C to RT, 90 min

Selectivity : 80:20 E/Z
See the Julia-Kociensky Olefination
Chemical structure
n-Bu4N+ F-
THF
RT, 2 h, 74% (2 steps)

Also isolated was 18 % of the Z-isomer.
Chemical structure
H2Cr2O7.2Pyr, Celite ®
4 Å MS
CH2Cl2
RT, 2 h, 87%
Chemical structure + Chemical structure
NaH
DME
0 °C to RT, 5 h, 80%

See the Horner-Wadsworth-Emmons Reaction
Chemical structure

Report an error in this part

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