Synthesis of Hellannuol A

C15H22O3
Principal investigator | Erich L. Grimm |
---|---|
Publication year | 1994 |
Synthesis type | Total |
Number of steps | 11 (linear) |
References |
Part 1 of 1

BnBr,
NaOH
EtOH, H2O
Reflux, 5.5 h, 65%

LiAlH4
THF
0 °C to Reflux, 3.5 h

PBr3
Et2O
0 °C

PhSO2Na
DMF
RT, 15 h, 85% (3 steps)

Pd/C,
H2
EtOAc
100%


CH2N2
Et2O
70% (2 steps)

TMS2NLi
THF
0 °C to RT, 90 min, 87%

NaBH4
MeOH
0 °C, 90 min, 83%

Na(Hg)
MeOH
0 °C to RT, 16 h, 45%

NaSEt
DMF
150 °C, 16 h, 70%
