Synthesis of Bikaverin

Structure of Bikaverin

C20H14O8

Principal investigator	Derek H. R. Barton
Publication year	1975
Synthesis type	Total
Number of steps	11 (linear)
References	J. Chem. Soc., Chem. Commun. 1974, 646. J. Chem. Soc., Perkin Trans. 1 1976, 499.

Part 1 of 1

intermediate structure

Me3N+Bn HO-, MeCN

Dean-Stark

PhH

Reflux, 2 h, 82%

See the Aldol Condensation

intermediate structure

Pd/C, H2

1 atm

EtOH

RT, 93%

intermediate structure

+

intermediate structure

ZnCl2, HCl

PhNO2

RT, 4 d, 70%

See the Houben-Hoesch Reaction

intermediate structure

(CO2Et)2, NaOEt

PhH

RT, 4 h, 40%

See the Claisen Condensation

intermediate structure

TsOH

PhH

Reflux, 2 h, 90%

intermediate structure

Me2SO4, K2CO3

Acetone

Reflux, 2 h, 90%

See the Williamson Ether Synthesis

intermediate structure

KOH

EtOH

RT, 24 h

intermediate structure

SOCl2

DMF, PhH

Reflux, 3 h

intermediate structure

BF3.OEt2

CH2Cl2

RT to reflux, ON, 77% (3 steps)

See the Friedel-Crafts Acylation

intermediate structure

K2Cr2O7

AcOH

RT, 2.5 h, 58%

intermediate structure

LiI

MeCOt-Bu

Reflux, 5 h, 80%

intermediate structure

Report an error in this part