Synthesis of Zearalenone
C18H22O5
Principal investigator | Guy Solladié |
---|---|
Publication year | 1991 |
Synthesis type | Formal |
Number of steps | 16 (3 parts) |
References |
Part 1 of 3
+
TMS2NLi
HMPA, THF
-78 °C, 35 min, 77%
mCPBA
CH2Cl2
0 °C, 90%
PhMe
Reflux, 2 h, 94%
Part 2 of 3
+
i-Pr2NLi
THF
-78 to -40 °C, 90 min
CH2N2
Et2O, MeOH
0 °C, 75% (2 steps)
i-Bu2AlH,
ZnCl2
THF
-78 °C, 50 min, 80%
Imidazole,
TBSCl
DMF
RT, ON, 98%
Ni (Raney)
EtOH
RT, 60 min, 89%
Part 3 of 3
+
TMS2NLi
THF
-78 to 0 °C, 2.5 h, 62%
Na2HPO4,
Na(Hg)
MeOH
-20 °C, 18 h, 90%
HS(CH2)3SH,
BF3.OEt2
CH2Cl2
RT, 60 min, 78%
KOH
Ethylene Glycol, H2O
140 & deg;C, 2 h, 84%
(PhO)2P(O)Cl,
Et3N
THF
0 °C, 30 min
DMAP
PhH
80 °C, 23 h, 60% (2 steps)
CaCO3,
MeI
H2O, MeCN
RT, 4 d, 84%
Remaining...
22% (1 step)
"See: Tetrahedron 1968, 24, 2443."