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Named reactions

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Kinamycin C

"This paper is dedicated to Prof. James S. Panek on the occasion of his 50th birthday."

Chemical structure of Kinamycin_C
C24H20N2O10
Author John A. Porco, Jr.
Publication year 2006
Synthesis type Total synthesis
Number of steps 27 (3 parts)
Reference

Browse hundreds of other total syntheses.

Part 1 of 3
Chemical structure
MeOCH2Cl, i-Pr2NEt
CH2Cl2
0 °C to RT, 3 h, 85%
Chemical structure
Na2S2O4
Et2O, H2O
RT, 10 min
Chemical structure
MeOCH2Cl, i-Pr2NEt
CH2Cl2
0 °C to RT, 24 h, 70% (2 steps)
Chemical structure
(n-Bu3Sn)2, Pd(PPh3)4
PhMe
110 °C, 24 h, 70%

See the Stille Coupling
Chemical structure

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Part 2 of 3
Chemical structure
Me3O+ BF4-, Proton Sponge ®
4 Å MS
CH2Cl2
RT, 12 h, 85%
Chemical structure
NaBH4
EtOAc
0 °C, 60 min, 99%
Chemical structure
PhI(OAc)2
MeOH
0 °C to RT, 40 min
Chemical structure
HO(CH2)3OH, BF3.OEt2
Et2O, DME
0 °C to RT, 3.5 h, 80% (2 steps)
Chemical structure
TBSCl, Imidazole
CH2Cl2
RT, 6 h, 90%
Chemical structure
(CH2O)n, La(OTf)3, N(CH2CH2OH)3, Et3P
CH2Cl2
-78 to -20 °C, 6.5 h, 70%

See the Morita-Baylis-Hillman Reaction
Chemical structure
Ph3COOH, TMS2NNa, (+)-DIPT
4 Å MS
PhMe
-65 °C, 72 h, 94%

Selectivity : 95:05 er
Chemical structure
Me4N+ BH(OAc)3-
AcOH, MeCN
0 °C, 24 h, 90%

See the Evans-Saksena Reduction
Chemical structure
MsCl, 2,4,6-Collidine
CH2Cl2
0-5 °C, 8 h, 85%
Chemical structure
LiBHEt3
DCE
60 °C, 30 min, 95%
Chemical structure
K-10 Clay
CH2Cl2
RT, 4 h, 90%
Chemical structure

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Part 3 of 3
Chemical structure
+
Chemical structure
Pd2(dba)3, Ph3As, CuCl, i-Pr2NEt
MeCN
70 °C, 4 h, 70%
Chemical structure
LiBHEt3
THF
-78 °C, 60 min, 80%
Chemical structure
Ti(Oi-Pr)4, n-Bu4N+ OAc-
4 Å MS
CH2Cl2
RT, 10 h, 60%
Chemical structure
Ac2O
Pyr
RT, 2 h
Chemical structure
HF, Et3N
MeCN
RT, 12 h, 67% (2 steps)
Chemical structure
n-Pr4N+ RuO4-, NMO
CH2Cl2
0 °C to RT, 20 min

See the Ley-Griffith Oxidation
Chemical structure
NaClO2, 2-Methyl-2-butene, NaH2PO4
t-BuOH, H2O
RT, 12 h, 88% (2 steps)

See the Pinnick-Lindgren Oxidation
Chemical structure
(CF3CO)2O
4 Å MS
DCE
0 °C to RT, 60 min, 90%

See the Friedel-Crafts Acylation
Chemical structure
CBr4
i-PrOH
Reflux, 60 min
Chemical structure
Pd/C, O2
EtOAc
RT, 30 min, 70% (2 steps)
Chemical structure
TBSNHNHTBS, Sc(OTf)3
CH2Cl2
-78 °C to RT
Chemical structure
PhIF2, 2-Chloropyridine
4 Å MS
CH2Cl2
-78 °C to RT, 7 h, 35% (2 steps)
Chemical structure

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