Synthesis of Streptonigrone

Structure of Streptonigrone

C24H22N4O7

Principal investigatorDale L. Boger
Publication year1993
Synthesis typeTotal
Number of steps 18 (linear)
References
Part 1 of 1
intermediate structure + intermediate structure
NaOH
MeOH
57 °C, 6 h
intermediate structure
HCl
MeOH
RT, 5 h, 85%
intermediate structure
i-Pr2NLi, EtOAc
Hexane(s), THF
-78 °C to RT, 55 min, 71%
intermediate structure + intermediate structure
Piperidine
EtOH
Reflux, 60 min, 81%
intermediate structure
Et3N, MsNH2, TiCl4
CH2Cl2
0 °C to RT, 6.5 h, 75%
intermediate structure + intermediate structure
PhH
RT, 3 h
intermediate structure
KOt-Bu
THF
-30 °C, 60 min
intermediate structure
DDQ
CH2Cl2
RT, 60 min, 65% (3 steps)
intermediate structure
LiOH
DMSO, H2O
60 °C, 7 h, 97%
intermediate structure
MeOCH2Cl, NaH
DMF
0 °C to RT, 2 h, 96%
intermediate structure
LiOH
DMSO, H2O
130 °C, 6 h, 80%
intermediate structure
(PhO)2P(O)N3, Et3N
PhH
RT to Reflux, 7.5 h, 84%
intermediate structure
HBr
CH2Cl2
0 °C, 2 h, 80%
intermediate structure
n-Bu4N+ HSO4-
CH2Cl2, H2O
RT, 4 h, 69%
intermediate structure
NaOMe, Ti(Oi-Pr)4
THF
0 °C, 105 min, 44%
intermediate structure
NaN3
H2O, THF
RT, 21 h, 85%
intermediate structure
NaBH4
MeOH, THF
RT, 60 min, 86%
intermediate structure
H2, HBr, Pd/C
CF3CH2OH
80 °C, 60 min
"No yield reported."
intermediate structure