Synthesis of Bicyclohumulenone

C15H24O
Principal investigator | André B. Charette |
---|---|
Publication year | 1997 |
Synthesis type | Total |
Number of steps | 15 (linear) |
References |
Part 1 of 1


HCl
H2O, THF
Reflux, 3 h, 80%

LiAlH4
THF
Reflux, 12 h, 70%

NaIO4
H2O, THF
RT, 24 h, 100%



Imidazole,
TBDPSCl
DMF
RT, 45 min, 66%


CH2I2,
Et2Zn
CH2Cl2, DME
0 °C to RT, 105 min, 88%
"94:06 e.r."

Celite,
H2Cr2O7.2Pyr
4 A MS
CH2Cl2
RT, 16 h, 100%



n-Bu4N+ F-
THF
RT, 5 h, 100%

LiCl,
MsCl,
2,4,6-Collidine
DMF
0 °C, 3 h

Cs2CO3
DMF, THF
Reflux, 6 h, 85% (2 steps)

KOH
DMF, H2O, MeOH
RT to 140 °C, 90 min, 100%
