Synthesis of Zearalenone

Structure of Zearalenone

C18H22O5

Principal investigatorGuy Solladié
Publication year1991
Synthesis typeFormal
Number of steps 16 (3 parts)
References
Part 1 of 3
intermediate structure + intermediate structure
TMS2NLi
THF, HMPA
-78 °C, 35 min, 77%
intermediate structure
mCPBA
CH2Cl2
0 °C, , 90%
intermediate structure
PhMe
Reflux, 2 h, 94%
intermediate structure
Part 2 of 3
intermediate structure + intermediate structure
i-Pr2NLi
THF
-78 to -40 °C, 90 min
intermediate structure
CH2N2
Et2O, MeOH
0 °C, , 75% (2 steps)
intermediate structure
i-Bu2AlH, ZnCl2
THF
-78 °C, 50 min, 80%
intermediate structure
TBSCl, Imidazole
DMF
RT, ON, 98%
intermediate structure
Ni (Raney)
EtOH
RT, 60 min, 89%
intermediate structure
Part 3 of 3
intermediate structure + intermediate structure
TMS2NLi
THF
-78 to 0 °C, 2.5 h, 62%
intermediate structure
Na(Hg), Na2HPO4
MeOH
-20 °C, 18 h, 90%
intermediate structure
HS(CH2)3SH, BF3.OEt2
CH2Cl2
RT, 60 min, 78%
intermediate structure
KOH
Ethylene Glycol, H2O
140 & deg;C, 2 h, 84%
intermediate structure
(PhO)2P(O)Cl, Et3N
THF
0 °C, 30 min
intermediate structure
DMAP
PhH
80 °C, 23 h, 60% (2 steps)
intermediate structure
MeI, CaCO3
MeCN, H2O
RT, 4 d, 84%
intermediate structure
Remaining...
22% (1 step)
"See: Tetrahedron 1968, 24, 2443."
intermediate structure