Synthesis of Brasilenyne

C15H19ClO
Principal investigator | Scott E. Denmark |
---|---|
Publication year | 2002 |
Synthesis type | Total |
Number of steps | 20 (linear) |
References |
Part 1 of 1

BF3.OEt2,
EtCHO
Et2O
-30 to 0 °C, 2 h, 85%

BH3.THF
THF
0 °C, 3 h, 82%

Pyr,
TBSCl
CH2Cl2
RT, 4 h, 85%


TiCl4
CH2Cl2
-72 °C, 3 h


AgNO3,
NIS
DMF
RT, 10 min, 95%

AcOH,
KO2C-N=N-CO2K
i-PrOH, THF
RT, 5 h, 80%

AlMe3,
NHMeOMe.HCl
CH2Cl2
0 °C to RT, 2 h, 93%

Ag2O,
(4-MeOPh)CH2Cl
CH2Cl2
RT, 24 h, 82% (89% BRSM)

i-Bu2AlH
CH2Cl2
-73 °C, 3 h, 87%



Et3N
CH2Cl2
0 °C to RT, 30 min, 91%



DMAP,
Pyr,
TBSOTf
CH2Cl2
0 °C to RT, 2 h, 88%

DDQ
CH2Cl2, H2O
RT, 30 min, 84%



n-BuLi
THF
-74 °C to RT, 8.5 h, 71%
See the Peterson Olefination
"Also isolated was the E-isomer (12%)"

n-Bu4N+ F-
THF
0 °C, 90 min, 93%

