Synthesis of Upial

Structure of Upial

C15H20O3

Principal investigatorToshio Honda
Publication year2008
Synthesis typePartial
Number of steps 15 (linear)
References
Angew. Chem. Int. Ed. 2008, 47, 131.
Part 1 of 1
intermediate structure
Et3N, TMSCl
DMF
130 °C, 68 h
"The starting material is obtained in 5 steps from 2-methylcyclohexanone, see: Tetrahedron: Asymmetry 1995, 6, 1795."
intermediate structure
LiAlH4
THF
0 °C, 40 min
intermediate structure
BzCl, Pyr
CH2Cl2
0 °C, 60 min, 77% (3 steps)
intermediate structure
O2, Pd(OAc)2
DMSO
80 °C, 15 h, 91%
See the Saegusa-Ito Oxidation
intermediate structure
CuCN, VinylMgBr
THF
-78 to -40 °C, 40 min, 98%
See the Michael Addition
intermediate structure
PhNTf2, TMS2NNa
-78 to -40 °C, 2.5 h, 81%
intermediate structure
TMSCH2MgCl, NaOH, Pd(PPh3)4
H2O, MeOH, THF
Reflux, 75 min, 94%
See the Kumada-Corriu Coupling
intermediate structure
n-Pr4N+ RuO4-, NMO
4A MS
CH2Cl2
0 °C, 60 min, 75%
See the Ley-Griffith Oxidation
intermediate structure
TsOH
CHCl3
RT to reflux, 30 min, 96%
See the Hosomi-Sakurai Reaction
intermediate structure
NMO, n-Pr4N+ RuO4-
4A MS
CH2Cl2
RT, 90 min, 82%
See the Ley-Griffith Oxidation
intermediate structure
NaBH4
MeOH
0 °C, 20 min
intermediate structure
2,6-Lutidine, OsO4, NaIO4
Dioxane , H2O, t-BuOH
RT, 26 h, 96% (2 steps)
See the Lemieux-Johnson Oxidation
intermediate structure
Ag2CO3
PhH
Reflux, 60 min, 94%
intermediate structure
Allyl-I, LDA
THF
-78 to 0 °C, 70 min, 75%
intermediate structure
2,6-Lutidine, OsO4, NaIO4
Dioxane , H2O, t-BuOH
RT, 24 h, 67%
See the Lemieux-Johnson Oxidation
intermediate structure
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