Synthesis of Eudistomin C

Structure of Eudistomin C

C14H16BrN3O2S

Principal investigator	Tohru Fukuyama
Publication year	2005
Synthesis type	Total
Number of steps	18 (linear)
References	J. Am. Chem. Soc. 2005, 127, 15038.

Part 1 of 1

intermediate structure

NaNO2 , H2SO4
KI

H2O, MeCN

0 °C to RT, 15 min

See the Sandmeyer Reaction

intermediate structure

FeCl2, HCl, Fe

EtOH, H2O

80 °C, 2 h

intermediate structure

Pyr, (CF3CO)2O

CH2Cl2

0 °C, 62% (3 steps)

intermediate structure

+

intermediate structure

DEAD, Ph3P

PhH

5 °C to RT, 15 min, 90%

See the Mitsunobu Reaction

intermediate structure

Et3N, Pd(OAc)2, Et3NBn+ Cl-

DMF

80 °C, 30 min, 66%

See the Mizoroki-Heck Reaction

intermediate structure

Boc2O, DMAP

CH2Cl2

RT, 20 min, 100%

intermediate structure

Camphorsulfonic acid

CH2Cl2, MeOH

RT, 30 min, 97%

intermediate structure

+

intermediate structure

DEAD, Ph3P

PhH

5 °C to RT, 15 min, 100%

See the Mitsunobu Reaction

intermediate structure

Me2S

CH2Cl2, CF3CO2H

RT, 30 min, 97%

intermediate structure

K2CO3, PhSH

DMF

RT, 45 min, 94%

intermediate structure

+

intermediate structure

Cl2CHCO2H

PhMe

0 °C, 15 min, 100%

See the Pictet-Spengler Reaction

intermediate structure

n-BuLi
ClCO2CH(Cl)CH3

THF

-78 °C to RT, 45 min, 89%

intermediate structure

SO2Cl2

CH2Cl2

-78 °C to RT, 35 min

intermediate structure

i-Pr2NEt, AcSH

CH2Cl2

RT, 95% (2 steps)

intermediate structure

AcOH

H2O, THF

80 °C, 15 min, 61%

intermediate structure

i-Pr2NEt, MsCl

CH2Cl2

0 °C, 5 min, 98%

intermediate structure

K2CO3

MeOH

80 °C, 15 min, 65%

intermediate structure

BBr3

CH2Cl2

-78 °C to RT, 2.5 h, 78%

intermediate structure

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