Synthesis of Upial
C15H20O3
| Principal investigator | Hiroto Nagaoka |
|---|---|
| Publication year | 1993 |
| Synthesis type | Total |
| Number of steps | 32 (linear) |
| References |
Part 1 of 1
+
+
LDA
THF
-78 to -20 °C, 17.5 h, 79%
See the Michael Addition
"another diastereomer was also isolated (6% yield)"
LiAlH4
THF
0 °C to RT, 94%
TsCl,
Pyr
RT, 85%
H2Cr2O7.2Pyr
4A MS
CH2Cl2
RT, 90%
KOt-Bu
DMF, THF
0 °C, 1 h, 93%
LiAlH4
THF
85%
MsCl,
DMAP,
Pyr
0 °C to RT, 97%
NaIO4
MeCN
RT, 98%
Na
EtOH, NH3
-34 °C, 93%
SeO2,
HCO2H
Dioxane
60 °C, 90 min, 99%
NH3
H2O, MeOH
RT, 97%
H2Cr2O7.2Pyr
4A MS
CH2Cl2
RT, 85%
NaBH3CN,
HCl
H2O, MeOH, THF
0 °C, 98%
MeOCH2Cl,
i-Pr2NEt
98%
(PhS)2,
Pyr,
n-Bu3P
80 °C, 97%
NaHCO3,
mCPBA
CH2Cl2
-78 °C, 95%
i-Pr2NEt
1,2-Dichlorobenzene
140, 98%
H2Cr2O7.2Pyr
4A MS
CH2Cl2
RT, 83%
HCl
AcOH, H2O
RT, 71%
HCO2Ac,
Pyr
CH2Cl2
0 °C, 94%
HCO2H
Dioxane
RT, 87%
SmI2
HMPA, THF
RT, 30 min, 76%
- Thexylborane
- NaHCO3 , H2O , NaBO3
0 °C to RT, 2.5 h
TBDPSCl,
Et3N,
DMAP
DMF
40 °C
H2Cr2O7.2Pyr
4A MS
CH2Cl2
RT, 75% (3 steps)
n-Bu4N+ F-
AcOH, THF
RT
H2Cr2O7.2Pyr
4A MS
CH2Cl2
RT, 70% (2 steps)