Synthesis of Kinamycin F

Structure of Kinamycin F

C18H14N2O7

Principal investigator	Seth B. Herzon
Publication year	2010
Synthesis type	Total
Number of steps	17 (3 parts)
References	J. Am. Chem. Soc. 2010, 132, 2540.

Part 1 of 3

intermediate structure

Br2

AcOH

120 °C, 20 min

intermediate structure

+

intermediate structure

i-Pr2NEt, MeOCH2Cl

CH2Cl2

0 °C, 30 min, 50% (2 steps)

"Also isolated was the C7-bromo product (33 % yield)."

intermediate structure

Na2CO3

MeOH

65 °C, 30 min, 96%

intermediate structure

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Part 2 of 3

intermediate structure

Na

NH3, t-BuOH, THF

-78 to -33 °C, 45 min, 100%

See the Birch Reduction

intermediate structure

MsNH2, AD-mix B

H2O, t-BuOH, TBME

12 °C, 40 h, 55%

See the Sharpless Asymmetric Dihydroxylation

intermediate structure

2,2-Dimethoxypropane, Pyr.TsOH

DMF

RT, 60 min, 88%

intermediate structure

CsF, PhSeCl

DMF

-50 °C, 80 min, 69%

intermediate structure

Pyr, H2O2

CH2Cl2

RT, 15 min, 83%

"Cristallized twice to 99:01 er."

intermediate structure

CuI , TMSCH2MgCl
Et3N , TMSCl

HMPA, THF

-78 °C to RT, 2 h

See the Michael Addition

intermediate structure

Pd(OAc)2

MeCN

RT, 3 h, 88% (2 steps)

See the Saegusa-Ito Oxidation

intermediate structure

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Part 3 of 3

intermediate structure

+

intermediate structure

TASF

CH2Cl2

-78 °C, 5 min, 79%

See the Michael Addition

intermediate structure

Ag2CO3, Ph3P, Pd(OAc)2

PhMe

80 °C, 60 min, 66%

See the Mizoroki-Heck Reaction

intermediate structure

TfN3, i-Pr2NEt

MeCN

RT, 20 min, 99%

intermediate structure

TIPSOTf, i-Pr2NEt

CH2Cl2

0 °C, 20 min

intermediate structure

DMDO

CH2Cl2, MeOH

-40 °C, 15 min, 76% (2 steps)

See the Rubottom Oxidation

intermediate structure

BH3.THF

THF

-78 to -20 °C, 2 h, 58%

intermediate structure

HCl

MeOH

-12 to 0 °C, 7 h, 65%

intermediate structure

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