Synthesis of Kinamycin F

C18H14N2O7
Principal investigator | Seth B. Herzon |
---|---|
Publication year | 2010 |
Synthesis type | Total |
Number of steps | 17 (3 parts) |
References |
Part 1 of 3
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Br2
AcOH
120 °C, 20 min


i-Pr2NEt,
MeOCH2Cl
CH2Cl2
0 °C, 30 min, 50% (2 steps)
"Also isolated was the C7-bromo product (33 % yield)."

Na2CO3
MeOH
65 °C, 30 min, 96%

Part 2 of 3



2,2-Dimethoxypropane,
Pyr.TsOH
DMF
RT, 60 min, 88%

CsF,
PhSeCl
DMF
-50 °C, 80 min, 69%

Pyr,
H2O2
CH2Cl2
RT, 15 min, 83%
"Cristallized twice to 99:01 er."



Part 3 of 3
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TfN3,
i-Pr2NEt
MeCN
RT, 20 min, 99%

TIPSOTf,
i-Pr2NEt
CH2Cl2
0 °C, 20 min


BH3.THF
THF
-78 to -20 °C, 2 h, 58%

HCl
MeOH
-12 to 0 °C, 7 h, 65%
