Synthesis of Hellannuol A

Structure of Hellannuol A

C15H22O3

Principal investigatorErich L. Grimm
Publication year1994
Synthesis typeTotal
Number of steps 11 (linear)
References
Part 1 of 1
intermediate structure
BnBr, NaOH
EtOH, H2O
Reflux, 5.5 h, 65%
intermediate structure
LiAlH4
THF
0 °C to Reflux, 3.5 h
intermediate structure
PBr3
Et2O
0 °C
intermediate structure
PhSO2Na
DMF
RT, 15 h, 85% (3 steps)
intermediate structure
H2, Pd/C
EtOAc
100%
intermediate structure
NaOH, CHCl3
Acetone
Reflux
intermediate structure
CH2N2
Et2O
70% (2 steps)
intermediate structure
TMS2NLi
THF
0 °C to RT, 90 min, 87%
intermediate structure
NaBH4
MeOH
0 °C, 90 min, 83%
intermediate structure
Na(Hg)
MeOH
0 °C to RT, 16 h, 45%
intermediate structure
NaSEt
DMF
150 °C, 16 h, 70%
intermediate structure