Synthesis of Leuconoxine

C19H22N2O2
Principal investigator | Tanja Gaich |
---|---|
Publication year | 2015 |
Synthesis type | Total |
Number of steps | 17 (linear) |
References |
Part 1 of 1
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TsOH
Dean-Stark
PhH
Reflux, 10 h, 55%

- i-Pr2NLi , HMPA
- AllylBr
THF
-78 °C, 5.5 h, 54%
">95:05 d.r."

BF3.OEt2
EtOH, H2O
RT, 3 h, 82%

Et3N,
TMSOTf
CH2Cl2
0 °C to RT, 40 min

NBS
MeCN, THF
0 °C to RT, 30 min

Me2S
PhMe
80 °C, 18 h, 95% (3 steps)



CF3CO2H
RT, 60 min, 88%

i-Bu2AlH
CH2Cl2
-78 °C, 2 h



Mg
MeOH
0 °C to RT, 80 min, 85%

LiAlH4
Et2O, THF
0 °C to RT, 1 h


- BH3.Me2S
- H2O , NaBO3.4H2O
THF
0 °C to RT, 6.5 h, 51%

Na2CO3
hv
MeOH
RT, 9 h, 5.8%

