Synthesis of Streptonigrone

C24H22N4O7
Principal investigator | Marco A. Ciufolini |
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Publication year | 2007 |
Synthesis type | Total |
Number of steps | 19 (linear) |
References |
Part 1 of 1
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MeOH
Reflux, 15 h, 58%


POCl3
PhH
RT, 24 h, 88%

Et3N,
H2,
Pd/C
EtOAc
RT, 45 min, 100%


HCl
Dioxane , H2O
70 °C, 15 h, 78% (2 steps)





ICl,
K2CO3
DMF
RT, 16 h

BnCl,
Ag2CO3
PhH
RT, 3 d, 36% (2 steps)

- n-BuLi
- CO2
THF
-78 °C to RT, 30 min


LiOH
H2O, THF
RT, 60 min

BnOCH2Cl,
NaHCO3
THF
0 °C to RT, 18 h, 37% (4 steps)

(NH4)2Ce(NO3)6
H2O, MeCN
0 °C, 45 min, 93%

ICl,
NaN3
MeCN
-10 °C to RT, 4 h

NaN3
H2O, THF
RT, 15 h

Na2S2O4
H2O, MeOH
Reflux, 4 h, 40% (3 steps)

TMSI
MeCN
RT to 55 °C, 3.5 h, 67%
