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Named reactions

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Search synthesis

Kinamycin F

Chemical structure of Kinamycin_F
C18H14N2O7
Author Seth B. Herzon
Publication year 2010
Synthesis type Total synthesis
Number of steps 17 (3 parts)
Reference

Browse hundreds of other total syntheses.

Part 1 of 3
Chemical structure
Br2
AcOH
120 °C, 20 min

Selectivity : 66:33
Chemical structure
+
Chemical structure
MeOCH2Cl, i-Pr2NEt
CH2Cl2
0 °C, 30 min, 50% (2 steps)

Also isolated was the C7-bromo product (33 % yield).
Chemical structure
Na2CO3
MeOH
65 °C, 30 min, 96%
Chemical structure

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Part 2 of 3
Chemical structure
Na
NH3, t-BuOH, THF
-78 to -33 °C, 45 min, 100%

See the Birch Reduction
Chemical structure
AD-mix β, MsNH2
TBME, t-BuOH, H2O
12 °C, 40 h, 55%

Selectivity : 83:17 er
See the Sharpless Asymmetric Dihydroxylation
Chemical structure
2,2-Dimethoxypropane, Pyr.TsOH
DMF
RT, 60 min, 88%
Chemical structure
CsF, PhSeCl
DMF
-50 °C, 80 min, 69%
Chemical structure
H2O2, Pyr
CH2Cl2
RT, 15 min, 83%

Cristallized twice to 99:01 er.
Chemical structure
  1. TMSCH2MgCl, CuI
  2. TMSCl, Et3N
THF, HMPA
-78 °C to RT, 2 h

See the Michael Addition
Chemical structure
Pd(OAc)2
MeCN
RT, 3 h, 88% (2 steps)

See the Saegusa-Ito Oxidation
Chemical structure

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Part 3 of 3
Chemical structure
+
Chemical structure
TASF
CH2Cl2
-78 °C, 5 min, 79%

See the Michael Addition
Chemical structure
Pd(OAc)2, Ph3P, Ag2CO3
PhMe
80 °C, 60 min, 66%

See the Heck Coupling
Chemical structure
TfN3, i-Pr2NEt
MeCN
RT, 20 min, 99%
Chemical structure
TIPSOTf, i-Pr2NEt
CH2Cl2
0 °C, 20 min
Chemical structure
DMDO
CH2Cl2, MeOH
-40 °C, 15 min, 76% (2 steps)

See the Rubottom Oxidation
Chemical structure
BH3.THF
THF
-78 to -20 °C, 2 h, 58%
Chemical structure
HCl
MeOH
-12 to 0 °C, 7 h, 65%
Chemical structure

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