Synthesis of Upial

C15H20O3
Principal investigator | Hiroto Nagaoka |
---|---|
Publication year | 1993 |
Synthesis type | Total |
Number of steps | 32 (linear) |
References |
Part 1 of 1
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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)
