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Named reactions

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Search synthesis

Zearalenone

Chemical structure of Zearalenone
C18H22O5
Author Guy Solladié
Publication year 1991
Synthesis type Formal synthesis
Number of steps 16 (3 parts)
Reference

Browse hundreds of other total syntheses.

Part 1 of 3
Chemical structure
+
Chemical structure
TMS2NLi
THF, HMPA
-78 °C, 35 min, 77 %
Chemical structure
mCPBA
CH2Cl2
0 °C, 90 %
Chemical structure
PhMe
Reflux, 2 h, 94 %
Chemical structure

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Part 2 of 3
Chemical structure
+
Chemical structure
i-Pr2NLi
THF
-78 to -40 °C, 90 min
Chemical structure
CH2N2
Et2O, MeOH
0 °C, 75 % (2 steps)
Chemical structure
i-Bu2AlH, ZnCl2
THF
-78 °C, 50 min, 80 %

Selectivity : 99:01 dr
Chemical structure
TBSCl, Imidazole
DMF
RT, ON, 98 %
Chemical structure
Ni (Raney)
EtOH
RT, 60 min, 89 %
Chemical structure

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Part 3 of 3
Chemical structure
+
Chemical structure
TMS2NLi
THF
-78 to 0 °C, 2.5 h, 62 %
Chemical structure
Na(Hg), Na2HPO4
MeOH
-20 °C, 18 h, 90 %
Chemical structure
HS(CH2)3SH, BF3.OEt2
CH2Cl2
RT, 60 min, 78 %
Chemical structure
KOH
Ethylene Glycol, H2O
140 & deg;C, 2 h, 84 %
Chemical structure
(PhO)2P(O)Cl, Et3N
THF
0 °C, 30 min
Chemical structure
DMAP
PhH
80 °C, 23 h, 60 % (2 steps)
Chemical structure
MeI, CaCO3
MeCN, H2O
RT, 4 d, 84 %
Chemical structure

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Remaining...
22 % (1 step)

See: Tetrahedron 1968, 24, 2443.
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