Synthesis of Streptonigrone

C24H22N4O7
Principal investigator | Dale L. Boger |
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Publication year | 1993 |
Synthesis type | Total |
Number of steps | 18 (linear) |
References |
Part 1 of 1
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Et3N,
MsNH2,
TiCl4
CH2Cl2
0 °C to RT, 6.5 h, 75%



KOt-Bu
THF
-30 °C, 60 min

DDQ
CH2Cl2
RT, 60 min, 65% (3 steps)

LiOH
DMSO, H2O
60 °C, 7 h, 97%

NaH,
MeOCH2Cl
DMF
0 °C to RT, 2 h, 96%

LiOH
DMSO, H2O
130 °C, 6 h, 80%


HBr
CH2Cl2
0 °C, 2 h, 80%


n-Bu4N+ HSO4-
CH2Cl2, H2O
RT, 4 h, 69%

NaOMe,
Ti(Oi-Pr)4
THF
0 °C, 105 min, 44%

NaN3
H2O, THF
RT, 21 h, 85%

NaBH4
MeOH, THF
RT, 60 min, 86%

H2,
HBr,
Pd/C
CF3CH2OH
80 °C, 60 min
"No yield reported."
