Synthesis of Kinamycin C

Structure of Kinamycin C

C24H20N2O10

Principal investigatorJohn A. Porco, Jr.
Publication year2006
Synthesis typeTotal
Number of steps 27 (3 parts)
References
Part 1 of 3
intermediate structure
i-Pr2NEt, MeOCH2Cl
CH2Cl2
0 °C to RT, 3 h, 85%
intermediate structure
Na2S2O4
Et2O, H2O
RT, 10 min
intermediate structure
i-Pr2NEt, MeOCH2Cl
CH2Cl2
0 °C to RT, 24 h, 70% (2 steps)
intermediate structure
Pd(PPh3)4, (n-Bu3Sn)2
PhMe
110 °C, 24 h, 70%
See the Stille Coupling
intermediate structure
Part 2 of 3
intermediate structure
Me3O+BF4-, Proton Sponge
CH2Cl2
RT, 12 h, 85%
intermediate structure
NaBH4
EtOAc
0 °C, 60 min, 99%
intermediate structure
PhI(OAc)2
MeOH
0 °C to RT, 40 min
intermediate structure
BF3.OEt2, HO(CH2)3OH
DME, Et2O
0 °C to RT, 3.5 h, 80% (2 steps)
intermediate structure
Imidazole, TBSCl
CH2Cl2
RT, 6 h, 90%
intermediate structure
(CH2O)n, La(OTf)3, N(CH2CH2OH)3, Et3P
CH2Cl2
-78 to -20 °C, 6.5 h, 70%
intermediate structure
Ph3COOH, TMS2NNa, (+)-DIPT
PhMe
-65 °C, 72 h, 94%
intermediate structure
Me4N+ BH(OAc)3-
AcOH, MeCN
0 °C, 24 h, 90%
intermediate structure
MsCl, 2,4,6-Collidine
CH2Cl2
0-5 °C, 8 h, 85%
intermediate structure
LiBHEt3
DCE
60 °C, 30 min, 95%
intermediate structure
K-10 Clay
CH2Cl2
RT, 4 h, 90%
intermediate structure
Part 3 of 3
intermediate structure + intermediate structure
CuCl, i-Pr2NEt, Pd2(dba)3, Ph3As
MeCN
70 °C, 4 h, 70%
intermediate structure
LiBHEt3
THF
-78 °C, 60 min, 80%
intermediate structure
n-Bu4N+ OAc-, Ti(Oi-Pr)4
CH2Cl2
RT, 10 h, 60%
intermediate structure
Ac2O
Pyr
RT, 2 h
intermediate structure
Et3N, HF
MeCN
RT, 12 h, 67% (2 steps)
intermediate structure
NMO, n-Pr4N+ RuO4-
CH2Cl2
0 °C to RT, 20 min
intermediate structure
NaH2PO4, NaClO2, 2-Methyl-2-butene
H2O, t-BuOH
RT, 12 h, 88% (2 steps)
intermediate structure
(CF3CO)2O
DCE
0 °C to RT, 60 min, 90%
intermediate structure
CBr4
i-PrOH
Reflux, 60 min
intermediate structure
O2, Pd/C
EtOAc
RT, 30 min, 70% (2 steps)
intermediate structure
Sc(OTf)3, TBSNHNHTBS
CH2Cl2
-78 °C to RT
intermediate structure
PhIF2, 2-Chloropyridine
CH2Cl2
-78 °C to RT, 7 h, 35% (2 steps)
intermediate structure