Synthesis of Upial

Structure of Upial

C15H20O3

Principal investigatorHiroto Nagaoka
Publication year1993
Synthesis typeTotal
Number of steps 32 (linear)
References
Part 1 of 1
intermediate structure + intermediate structure
LDA
THF
-78 to -20 °C, 17.5 h, 79%
"another diastereomer was also isolated (6% yield)"
intermediate structure
LiAlH4
THF
0 °C to RT, 94%
intermediate structure
TsCl, Pyr
RT, 85%
intermediate structure
H2Cr2O7.2Pyr
4A MS
CH2Cl2
RT, 90%
intermediate structure
KOt-Bu
DMF, THF
0 °C, 1 h, 93%
intermediate structure
LiAlH4
THF
85%
intermediate structure
MsCl, DMAP, Pyr
0 °C to RT, 97%
intermediate structure
HCl
H2O, MeCN
RT, 24 h, 91%
intermediate structure
NaIO4
MeCN
RT, 98%
intermediate structure
Na
EtOH, NH3
-34 °C, 93%
intermediate structure
NaH, BnBr
DMF
RT, 99%
intermediate structure
SeO2, HCO2H
Dioxane
60 °C, 90 min, 99%
intermediate structure
NH3
H2O, MeOH
RT, 97%
intermediate structure
H2Cr2O7.2Pyr
4A MS
CH2Cl2
RT, 85%
intermediate structure
Me2CuLi
Et2O
-78 to -34 °C, 99%
intermediate structure
NaBH3CN, HCl
H2O, MeOH, THF
0 °C, 98%
intermediate structure
MeOCH2Cl, i-Pr2NEt
98%
intermediate structure
Na
EtOH, NH3, THF
-34 °C, 95%
See the Birch Reduction
intermediate structure
(PhS)2, Pyr, n-Bu3P
80 °C, 97%
intermediate structure
NaHCO3, mCPBA
CH2Cl2
-78 °C, 95%
intermediate structure
i-Pr2NEt
1,2-Dichlorobenzene
140, 98%
intermediate structure
H2Cr2O7.2Pyr
4A MS
CH2Cl2
RT, 83%
intermediate structure
HCl
AcOH, H2O
RT, 71%
intermediate structure
VinylMgBr
Et2O
0 °C to RT, 87%
intermediate structure
HCO2Ac, Pyr
CH2Cl2
0 °C, 94%
intermediate structure
HCO2H
Dioxane
RT, 87%
intermediate structure
SmI2
HMPA, THF
RT, 30 min, 76%
intermediate structure
  1. Thexylborane
  2. NaHCO3 , H2O , NaBO3
0 °C to RT, 2.5 h
intermediate structure
TBDPSCl, Et3N, DMAP
DMF
40 °C
intermediate structure
H2Cr2O7.2Pyr
4A MS
CH2Cl2
RT, 75% (3 steps)
intermediate structure
n-Bu4N+ F-
AcOH, THF
RT
intermediate structure
H2Cr2O7.2Pyr
4A MS
CH2Cl2
RT, 70% (2 steps)
intermediate structure