| Autor: |
Cornforth, J, Hawes, JE, Mallaby, R |
| Zdroj: |
Australian Journal of Chemistry; 1992, Vol. 45 Issue: 1 p179-185, 7p |
| Abstrakt: |
A convenient separation of (E)- and (Z)-3-methylpent-2-enedioic acids was devised, and it was shown that with acetyl chloride or thionyl chloride the (Z)-acid yields the cyclic anhydride while the (E)-acid forms 6-chloro-4-methylpyran-2-one. The chloropyranone by conventional chemistry gave 4-methyl-6-(2′-oxopropyl)pyran-2-one which condensed with 4-methylpent-3-en-2-one in the presence of pyrrolidine, yielding 4-methyl-6-(2′,6′,6′-trimethyl-4′-oxocyclohex-2′-enyl)pyran-2-one. Oxidation with selenium dioxide or t-butyl chromate then gave 6-(1′-hydroxy-2′,6′,6′-trimethyl-4′-oxotyclohex-2′-enyl)-4-methylpyran-2-one, which on reduction by lithium aluminium hydride and reoxidation afforded ()-abscisic acid stereospecifically. |
| Databáze: |
Supplemental Index |
| Externí odkaz: |
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