Synthesis of Kinamycin C

Structure of Kinamycin C

C24H20N2O10

Principal investigator	John A. Porco, Jr.
Publication year	2006
Synthesis type	Total
Number of steps	27 (3 parts)
References	J. Am. Chem. Soc. 2006, 128, 14790.

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

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Part 2 of 3

intermediate structure

Me3O+BF4-, Proton Sponge

4 Å MS

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

Et3P, N(CH2CH2OH)3, La(OTf)3, (CH2O)n

CH2Cl2

-78 to -20 °C, 6.5 h, 70%

See the Morita-Baylis-Hillman Reaction

intermediate structure

Ph3COOH, TMS2NNa, (+)-DIPT

4 Å MS

PhMe

-65 °C, 72 h, 94%

intermediate structure

Me4N+ BH(OAc)3-

AcOH, MeCN

0 °C, 24 h, 90%

See the Evans-Saksena Reduction

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

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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

4 Å MS

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

n-Pr4N+ RuO4-, NMO

CH2Cl2

0 °C to RT, 20 min

See the Ley-Griffith Oxidation

intermediate structure

NaClO2, 2-Methyl-2-butene, NaH2PO4

H2O, t-BuOH

RT, 12 h, 88% (2 steps)

See the Pinnick-Lindgren Oxidation

intermediate structure

(CF3CO)2O

4 Å MS

DCE

0 °C to RT, 60 min, 90%

See the Friedel-Crafts Acylation

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

4 Å MS

CH2Cl2

-78 °C to RT, 7 h, 35% (2 steps)

intermediate structure

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