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Named reactions

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Search synthesis

Streptonigrone

Chemical structure of Streptonigrone
C24H22N4O7
Author Dale L. Boger
Publication year 1993
Synthesis type Total synthesis
Number of steps 18 (linear)
Reference

Browse hundreds of other total syntheses.

Part 1 of 1
Chemical structure
+
Chemical structure
NaOH
MeOH
57 °C, 6 h

See the Friedländer synthesis
Chemical structure
HCl
MeOH
RT, 5 h, 85%

See the Fischer Esterification
Chemical structure
i-Pr2NLi, EtOAc
THF, Hexane(s)
-78 °C to RT, 55 min, 71%

See the Claisen Condensation
Chemical structure + Chemical structure
Piperidine
EtOH
Reflux, 60 min, 81%

See the Knoevenagel Condensation
Chemical structure
MsNH2, TiCl4, Et3N
CH2Cl2
0 °C to RT, 6.5 h, 75%
Chemical structure + Chemical structure
PhH
RT, 3 h

See the Diels-Alder Reaction
Chemical structure
KOt-Bu
THF
-30 °C, 60 min
Chemical structure
DDQ
CH2Cl2
RT, 60 min, 65% (3 steps)
Chemical structure
LiOH
DMSO, H2O
60 °C, 7 h, 97%
Chemical structure
MeOCH2Cl, NaH
DMF
0 °C to RT, 2 h, 96%
Chemical structure
LiOH
DMSO, H2O
130 °C, 6 h, 80%
Chemical structure
(PhO)2P(O)N3, Et3N
PhH
RT to Reflux, 7.5 h, 84%

See the Curtius Rearrangement
Chemical structure
HBr
CH2Cl2
0 °C, 2 h, 80%
Chemical structure
Reagent structure
n-Bu4N+ HSO4-
CH2Cl2, H2O
RT, 4 h, 69%
Chemical structure
NaOMe, Ti(Oi-Pr)4
THF
0 °C, 105 min, 44%
Chemical structure
NaN3
THF, H2O
RT, 21 h, 85%
Chemical structure
NaBH4
THF, MeOH
RT, 60 min, 86%
Chemical structure
H2, Pd/C, HBr
CF3CH2OH
80 °C, 60 min

No yield reported.
Chemical structure

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