Synthesis of Zearalenone

Structure of Zearalenone

C18H22O5

Principal investigator	Guy Solladié
Publication year	1991
Synthesis type	Formal
Number of steps	16 (3 parts)
References	J. Org. Chem. 1991, 56, 2317.

Part 1 of 3

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+

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TMS2NLi

HMPA, THF

-78 °C, 35 min, 77%

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mCPBA

CH2Cl2

0 °C, 90%

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PhMe

Reflux, 2 h, 94%

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Part 2 of 3

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+

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i-Pr2NLi

THF

-78 to -40 °C, 90 min

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CH2N2

Et2O, MeOH

0 °C, 75% (2 steps)

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i-Bu2AlH, ZnCl2

THF

-78 °C, 50 min, 80%

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Imidazole, TBSCl

DMF

RT, ON, 98%

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Ni (Raney)

EtOH

RT, 60 min, 89%

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Part 3 of 3

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+

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TMS2NLi

THF

-78 to 0 °C, 2.5 h, 62%

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Na2HPO4, Na(Hg)

MeOH

-20 °C, 18 h, 90%

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HS(CH2)3SH, BF3.OEt2

CH2Cl2

RT, 60 min, 78%

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KOH

Ethylene Glycol, H2O

140 & deg;C, 2 h, 84%

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(PhO)2P(O)Cl, Et3N

THF

0 °C, 30 min

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DMAP

PhH

80 °C, 23 h, 60% (2 steps)

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CaCO3, MeI

H2O, MeCN

RT, 4 d, 84%

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Remaining...

22% (1 step)

"See: Tetrahedron 1968, 24, 2443."

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