Jasmone 1 - ChemistforChrist
Jasmone 1 - ChemistforChrist
Jasmone 1 - ChemistforChrist
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Synthesis of JASMONE<br />
Cope Rearrangement<br />
1 2<br />
1<br />
2<br />
3<br />
4<br />
5<br />
Cope<br />
2<br />
1 2<br />
1<br />
3 4<br />
Synthesis of Descotes Synthesis 1975, 118-119<br />
3<br />
O<br />
3<br />
4<br />
2 6<br />
H<br />
1<br />
5<br />
4<br />
2 6<br />
H<br />
1<br />
CO 2Et<br />
CO 2Et<br />
5<br />
much<br />
cheaper<br />
5<br />
H<br />
Z<br />
Cope<br />
O O<br />
YZn X<br />
CH2<br />
EtO 2C CO 2Et<br />
CO 2Et<br />
EtO 2C CO 2Et K 2CO 3 EtO 2C CO 2Et Br<br />
Br<br />
+<br />
Br<br />
EtO 2C CO 2Et<br />
2 steps as<br />
explained above<br />
(Grignard, Oxidation)<br />
CO 2Et<br />
+ K 2CO 3<br />
intramolecular<br />
reaction<br />
(ring closure)<br />
More resources available at<br />
www.chemistforchrist.de<br />
Simmons Smith<br />
Br EtO 2C CO 2Et<br />
Technique to enlarge<br />
cyclic systems<br />
Br<br />
<strong>Jasmone</strong><br />
K 2CO 3<br />
EtO 2C CO 2Et<br />
Br
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