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Named reactions

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Kinamycin F

"Dedicated to George A. Olah on the occasion of his 80th birthday."

Chemical structure of Kinamycin_F
C18H14N2O7
Author Kyriacos C. Nicolaou
Publication year 2007
Synthesis type Total synthesis
Number of steps 27 (3 parts)
Reference

Browse hundreds of other total syntheses.

Part 1 of 3
Chemical structure
+
Chemical structure
AgNO3, (NH4)2S2O8
MeCN, H2O
65 °C, 3.5 h, 75%
Chemical structure
BnBr, Ag2O
CH2Cl2
RT, 18 h, 92%
Chemical structure
Na2S2O4
Et2O, EtOAc, H2O
RT, 30 min
Chemical structure
NaH, MeI
DMF
-15 °C, 60 min, 82% (2 steps)

See the Williamson Ether Synthesis
Chemical structure
KOt-Bu
THF
0 °C, 2 h, 98%
Chemical structure
OsO4, NaIO4
THF, H2O
70 °C, 18 h, 84%

See the Lemieux-Johnson Oxidation
Chemical structure

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Part 2 of 3
Chemical structure
  1. MeMgBr, CuBr.Me2S
  2. TMSCl
THF, HMPA
-78 °C to RT, 2.5 h

See the Michael Addition
The starting material was 90:10 er.
Chemical structure
Pd(OAc)2, O2
DMSO
RT, 18 h, 90% (2 steps)

See the Saegusa-Ito Oxidation
Chemical structure
OsO4, NMO
Acetone, H2O
RT, 45 min, 76%

See the Upjohn Dihydroxylation
Cristallized thrice to >99:01 er.
Chemical structure
2-Methoxypropene, Camphorsulfonic acid
THF
RT, 18 h, 95%
Chemical structure
  1. TMS2NLi
  2. TMSCl
THF
0 °C, 30 min
Chemical structure
Pd(OAc)2, O2
DMSO
RT, 18 h, 84% (2 steps)

See the Saegusa-Ito Oxidation
Chemical structure
I2
Pyr, CH2Cl2
RT, 30 min, 92%
Chemical structure

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Part 3 of 3
Chemical structure
+
Chemical structure
Cu, CuI, Pd2(dba)3
DMSO
65 °C, 2.5 h, 83%

See the Ullmann Coupling
Chemical structure
Reagent structure
Et3N
CH2Cl2
45 °C, 4 h, 78%

See the Benzoin Condensation
Chemical structure
Ac2O, Et3N, DMAP
CH2Cl2
RT, 20 h, 95%
Chemical structure
SmI2, MeOH
THF
-78 °C, 10 min
Chemical structure
Et3N
CH2Cl2
RT, 60 min, 81% (2 steps)
Chemical structure
SeO2
Dioxane
110 °C, 9 h, 72%
Chemical structure
HF
MeCN, H2O
RT, 3 h
Chemical structure
Ac2O, Et3N, DMAP
CH2Cl2
RT, 20 min, 89% (2 steps)
Chemical structure
H2, Pd/C
1 atm
EtOAc, AcOH
RT, 3 h, 99%
Chemical structure
TBSCl, Imidazole
DMF
RT, 3 h, 94%
Chemical structure
TsNHNH2, HCl
i-PrOH, H2O
RT, 18 h, 95%
Chemical structure
(NH4)2Ce(NO3)6
MeCN, Buffer (pH = 7)
0 °C, 60 min, 42%
Chemical structure
HCl
MeCN, H2O
RT, 3 h, 95%
Chemical structure
LiOH
THF, H2O
RT, 60 min, 92%
Chemical structure

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