Synthesis of Upial

C15H20O3
Principal investigator | Toshio Honda |
---|---|
Publication year | 2008 |
Synthesis type | Partial |
Number of steps | 15 (linear) |
References |
Part 1 of 1

Et3N,
TMSCl
DMF
130 °C, 68 h
"The starting material is obtained in 5 steps from 2-methylcyclohexanone, see: Tetrahedron: Asymmetry 1995, 6, 1795."

LiAlH4
THF
0 °C, 40 min

BzCl,
Pyr
CH2Cl2
0 °C, 60 min, 77% (3 steps)



PhNTf2,
TMS2NNa
-78 to -40 °C, 2.5 h, 81%





NaBH4
MeOH
0 °C, 20 min

2,6-Lutidine,
OsO4,
NaIO4
Dioxane , H2O, t-BuOH
RT, 26 h, 96% (2 steps)
See the Lemieux-Johnson Oxidation

Ag2CO3
PhH
Reflux, 60 min, 94%

Allyl-I,
LDA
THF
-78 to 0 °C, 70 min, 75%

