Synthesis of Aflatoxin B1

Structure of Aflatoxin B1

C17H12O6

Principal investigator	Barry M. Trost
Publication year	2003
Synthesis type	Total
Number of steps	9 (linear)
References	J. Am. Chem. Soc. 2003, 125, 3090.

Part 1 of 1

intermediate structure

+

intermediate structure

HCl

EtOH

RT, 72 h, 47%

See the Pechmann Condensation

intermediate structure

ICl

CH2Cl2

RT, 30 min, 92%

intermediate structure

+

intermediate structure

Special reagent

n-Bu4N+ Cl-, Pd2(dba)3.CHCl3

CH2Cl2

RT, 12 h, 89%

See the Trost Asymmetic Allylation Alkylation

intermediate structure

PdCl2.2MeCN, HCO2H

DMF, Et3N

60 °C, 60 min, 93%

See the Mizoroki-Heck Reaction

intermediate structure

HCl

AcOH, H2O

RT, 48 h

intermediate structure

Sc(OTf)3, LiClO4

MeNO2

60 °C, 4 h, 32% (2 steps)

See the Friedel-Crafts Acylation

intermediate structure

i-Bu2AlH

CH2Cl2

-78 °C, 60 min, 57%

intermediate structure

Ac2O

AcOH

RT, 20 h

intermediate structure

PhMe

240 °C, 15 min, 24% (2 steps)

intermediate structure

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