Synthesis of Kinamycin F

Structure of Kinamycin F

C18H14N2O7

Principal investigatorSeth B. Herzon
Publication year2010
Synthesis typeTotal
Number of steps 17 (3 parts)
References
Part 1 of 3
intermediate structure
Br2
AcOH
120 °C, 20 min
intermediate structure + intermediate structure
i-Pr2NEt, MeOCH2Cl
CH2Cl2
0 °C, 30 min, 50% (2 steps)
"Also isolated was the C7-bromo product (33 % yield)."
intermediate structure
Na2CO3
MeOH
65 °C, 30 min, 96%
intermediate structure
Part 2 of 3
intermediate structure
Na
NH3, t-BuOH, THF
-78 to -33 °C, 45 min, 100%
See the Birch Reduction
intermediate structure
AD-mix B, MsNH2
H2O, t-BuOH, TBME
12 °C, 40 h, 55%
intermediate structure
Pyr.TsOH, 2,2-Dimethoxypropane
DMF
RT, 60 min, 88%
intermediate structure
PhSeCl, CsF
DMF
-50 °C, 80 min, 69%
intermediate structure
H2O2, Pyr
CH2Cl2
RT, 15 min, 83%
"Cristallized twice to 99:01 er."
intermediate structure
  1. CuI
  2. Et3N
  3. TMSCl
  4. TMSCH2MgCl
HMPA, THF
-78 °C to RT, 2 h
intermediate structure
Pd(OAc)2
MeCN
RT, 3 h, 88% (2 steps)
intermediate structure
Part 3 of 3
intermediate structure + intermediate structure
TASF
CH2Cl2
-78 °C, 5 min, 79%
intermediate structure
Pd(OAc)2, Ph3P, Ag2CO3
PhMe
80 °C, 60 min, 66%
See the Heck Coupling
intermediate structure
i-Pr2NEt, TfN3
MeCN
RT, 20 min, 99%
intermediate structure
i-Pr2NEt, TIPSOTf
CH2Cl2
0 °C, 20 min
intermediate structure
DMDO
CH2Cl2, MeOH
-40 °C, 15 min, 76% (2 steps)
intermediate structure
BH3.THF
THF
-78 to -20 °C, 2 h, 58%
intermediate structure
HCl
MeOH
-12 to 0 °C, 7 h, 65%
intermediate structure