Synthesis of Leuconoxine

Structure of Leuconoxine

C19H22N2O2

Principal investigatorTanja Gaich
Publication year2015
Synthesis typeTotal
Number of steps 17 (linear)
References
Chem. Eur. J. 2015, 21, 6355.
Part 1 of 1
intermediate structure + intermediate structure
TsOH
Dean-Stark
PhH
Reflux, 10 h, 55%
intermediate structure
  1. i-Pr2NLi , HMPA
  2. AllylBr
THF
-78 °C, 5.5 h, 54%
">95:05 d.r."
intermediate structure
BF3.OEt2
EtOH, H2O
RT, 3 h, 82%
intermediate structure
Et3N, TMSOTf
CH2Cl2
0 °C to RT, 40 min
intermediate structure
NBS
MeCN, THF
0 °C to RT, 30 min
intermediate structure
Me2S
PhMe
80 °C, 18 h, 95% (3 steps)
intermediate structure
  1. t-BuOCl , PhNH2
  2. Et3N
CH2Cl2, MeCN
-45 °C to RT, 3 h, 77%
See the Gassman indole synthesis
intermediate structure
Special reagent
CF3CO2H
RT, 60 min, 88%
intermediate structure
i-Bu2AlH
CH2Cl2
-78 °C, 2 h
intermediate structure
Et3N, Pyr.SO3
DMSO
RT, 30 min
See the Parikh-Doering Oxidation
intermediate structure
Ph3P=CHCN
PhMe
80 °C, 2 h, 73% (3 steps)
See the Wittig Reaction
intermediate structure
Mg
MeOH
0 °C to RT, 80 min, 85%
intermediate structure
LiAlH4
Et2O, THF
0 °C to RT, 1 h
intermediate structure
DMAP, ClCH2CO2H, DIC
CH2Cl2
0 °C to RT, 60 min, 73% (3 steps)
See the Steglich Esterification
intermediate structure
  1. BH3.Me2S
  2. H2O , NaBO3.4H2O
THF
0 °C to RT, 6.5 h, 51%
intermediate structure
Na2CO3
hv
MeOH
RT, 9 h, 5.8%
intermediate structure
NMO, n-Pr4N+ RuO4-
MeCN
0 °C to RT
See the Ley-Griffith Oxidation
intermediate structure
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