Synthesis of Kinamycin F

Structure of Kinamycin F

C18H14N2O7

Principal investigatorKyriacos C. Nicolaou
Publication year2007
Synthesis typeTotal
Number of steps 27 (3 parts)
References
J. Am. Chem. Soc. 2007, 129, 10356.
Part 1 of 3
intermediate structure + intermediate structure
AgNO3, (NH4)2S2O8
H2O, MeCN
65 °C, 3.5 h, 75%
intermediate structure
Ag2O, BnBr
CH2Cl2
RT, 18 h, 92%
intermediate structure
Na2S2O4
Et2O, EtOAc, H2O
RT, 30 min
intermediate structure
NaH, MeI
DMF
-15 °C, 60 min, 82% (2 steps)
See the Williamson Ether Synthesis
intermediate structure
KOt-Bu
THF
0 °C, 2 h, 98%
intermediate structure
OsO4, NaIO4
H2O, THF
70 °C, 18 h, 84%
See the Lemieux-Johnson Oxidation
intermediate structure
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Part 2 of 3
intermediate structure
  1. CuBr.Me2S , MeMgBr
  2. TMSCl
HMPA, THF
-78 °C to RT, 2.5 h
See the Michael Addition
"The starting material was 90:10 er."
intermediate structure
Pd(OAc)2, O2
DMSO
RT, 18 h, 90% (2 steps)
See the Saegusa-Ito Oxidation
intermediate structure
OsO4, NMO
Acetone, H2O
RT, 45 min, 76%
See the Upjohn Dihydroxylation
"Cristallized thrice to >99:01 er."
intermediate structure
2-Methoxypropene, Camphorsulfonic acid
THF
RT, 18 h, 95%
intermediate structure
  1. TMS2NLi
  2. TMSCl
THF
0 °C, 30 min
intermediate structure
Pd(OAc)2, O2
DMSO
RT, 18 h, 84% (2 steps)
See the Saegusa-Ito Oxidation
intermediate structure
I2
CH2Cl2, Pyr
RT, 30 min, 92%
intermediate structure
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Part 3 of 3
intermediate structure + intermediate structure
CuI, Pd2(dba)3, Cu
DMSO
65 °C, 2.5 h, 83%
See the Ullmann Coupling
intermediate structure
Special reagent
Et3N
CH2Cl2
45 °C, 4 h, 78%
See the Benzoin Condensation
intermediate structure
Ac2O, DMAP, Et3N
CH2Cl2
RT, 20 h, 95%
intermediate structure
SmI2, MeOH
THF
-78 °C, 10 min
intermediate structure
Et3N
CH2Cl2
RT, 60 min, 81% (2 steps)
intermediate structure
SeO2
Dioxane
110 °C, 9 h, 72%
intermediate structure
HF
H2O, MeCN
RT, 3 h
intermediate structure
DMAP, Et3N, Ac2O
CH2Cl2
RT, 20 min, 89% (2 steps)
intermediate structure
H2, Pd/C
1 atm
AcOH, EtOAc
RT, 3 h, 99%
intermediate structure
Imidazole, TBSCl
DMF
RT, 3 h, 94%
intermediate structure
HCl, TsNHNH2
H2O, i-PrOH
RT, 18 h, 95%
intermediate structure
(NH4)2Ce(NO3)6
MeCN, Buffer (pH = 7)
0 °C, 60 min, 42%
intermediate structure
HCl
H2O, MeCN
RT, 3 h, 95%
intermediate structure
LiOH
H2O, THF
RT, 60 min, 92%
intermediate structure
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