Synthesis of Streptonigrone

Structure of Streptonigrone

C24H22N4O7

Principal investigatorMarco A. Ciufolini
Publication year2007
Synthesis typeTotal
Number of steps 19 (linear)
References
J. Org. Chem. 2007, 72, 8489.
Part 1 of 1
intermediate structure + intermediate structure
MeOH
Reflux, 15 h, 58%
intermediate structure
Ph2O
Reflux, 2 h, 86%
See the Conrad-Limpach Synthesis
intermediate structure
POCl3
PhH
RT, 24 h, 88%
intermediate structure
Et3N, H2, Pd/C
EtOAc
RT, 45 min, 100%
intermediate structure
NaH, EtOAc
PhMe
110 °C, 15 h
See the Claisen Condensation
intermediate structure
HCl
Dioxane , H2O
70 °C, 15 h, 78% (2 steps)
intermediate structure + intermediate structure
NaOH
EtOH, H2O
RT, 15 h, 83%
See the Claisen-Schmidt Condensation
intermediate structure + intermediate structure
KOt-Bu
DMSO
RT to 100 °C, 10 h, 60%
See the Michael Addition
intermediate structure
ICl, K2CO3
DMF
RT, 16 h
intermediate structure
BnCl, Ag2CO3
PhH
RT, 3 d, 36% (2 steps)
intermediate structure
  1. n-BuLi
  2. CO2
THF
-78 °C to RT, 30 min
intermediate structure
(PhO)2P(O)N3, Et3N
THF
Reflux, 15 h
See the Curtius Rearrangement
intermediate structure
LiOH
H2O, THF
RT, 60 min
intermediate structure
BnOCH2Cl, NaHCO3
THF
0 °C to RT, 18 h, 37% (4 steps)
intermediate structure
(NH4)2Ce(NO3)6
H2O, MeCN
0 °C, 45 min, 93%
intermediate structure
ICl, NaN3
MeCN
-10 °C to RT, 4 h
intermediate structure
NaN3
H2O, THF
RT, 15 h
intermediate structure
Na2S2O4
H2O, MeOH
Reflux, 4 h, 40% (3 steps)
intermediate structure
TMSI
MeCN
RT to 55 °C, 3.5 h, 67%
intermediate structure
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