Synthesis of Kinamycin C

C24H20N2O10
Principal investigator | John A. Porco, Jr. |
---|---|
Publication year | 2006 |
Synthesis type | Total |
Number of steps | 27 (3 parts) |
References |
Part 1 of 3

i-Pr2NEt,
MeOCH2Cl
CH2Cl2
0 °C to RT, 3 h, 85%

Na2S2O4
Et2O, H2O
RT, 10 min

i-Pr2NEt,
MeOCH2Cl
CH2Cl2
0 °C to RT, 24 h, 70% (2 steps)


Part 2 of 3

Me3O+BF4-,
Proton Sponge
4 Å MS
CH2Cl2
RT, 12 h, 85%

NaBH4
EtOAc
0 °C, 60 min, 99%

PhI(OAc)2
MeOH
0 °C to RT, 40 min

BF3.OEt2,
HO(CH2)3OH
DME, Et2O
0 °C to RT, 3.5 h, 80% (2 steps)

Imidazole,
TBSCl
CH2Cl2
RT, 6 h, 90%

Et3P,
N(CH2CH2OH)3,
La(OTf)3,
(CH2O)n
CH2Cl2
-78 to -20 °C, 6.5 h, 70%
See the Morita-Baylis-Hillman Reaction

Ph3COOH,
TMS2NNa,
(+)-DIPT
4 Å MS
PhMe
-65 °C, 72 h, 94%


MsCl,
2,4,6-Collidine
CH2Cl2
0-5 °C, 8 h, 85%

LiBHEt3
DCE
60 °C, 30 min, 95%

K-10 Clay
CH2Cl2
RT, 4 h, 90%

Part 3 of 3
+


CuCl,
i-Pr2NEt,
Pd2(dba)3,
Ph3As
MeCN
70 °C, 4 h, 70%

LiBHEt3
THF
-78 °C, 60 min, 80%

n-Bu4N+ OAc-,
Ti(Oi-Pr)4
4 Å MS
CH2Cl2
RT, 10 h, 60%

Ac2O
Pyr
RT, 2 h

Et3N,
HF
MeCN
RT, 12 h, 67% (2 steps)


NaClO2,
2-Methyl-2-butene,
NaH2PO4
H2O, t-BuOH
RT, 12 h, 88% (2 steps)
See the Pinnick-Lindgren Oxidation


CBr4
i-PrOH
Reflux, 60 min

O2,
Pd/C
EtOAc
RT, 30 min, 70% (2 steps)

Sc(OTf)3,
TBSNHNHTBS
CH2Cl2
-78 °C to RT

PhIF2,
2-Chloropyridine
4 Å MS
CH2Cl2
-78 °C to RT, 7 h, 35% (2 steps)
