
TY  - JOUR
A1  - Cornforth, J 
A1  - Hawes, JE 
A1  - Mallaby, R 
T1  - A Stereospecific Synthesis of (&#xb1;)-Abscisic Acid
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1992
VL  - 45
IS  - 1
SP  - 179
EP  - 185
KW  - 
UR  - https://doi.org/10.1071/CH9920179 
N2  - 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&#x2032;-oxopropyl)pyran-2-one which condensed with 4-methylpent-3-en-2-one in the presence of pyrrolidine, yielding 4-methyl-6-(2&#x2032;,6&#x2032;,6&#x2032;-trimethyl-4&#x2032;-oxocyclohex-2&#x2032;-enyl)pyran-2-one. Oxidation with selenium dioxide or t-butyl chromate then gave 6-(1&#x2032;-hydroxy-2&#x2032;,6&#x2032;,6&#x2032;-trimethyl-4&#x2032;-oxotyclohex-2&#x2032;-enyl)-4-methylpyran-2-one, which on reduction by lithium aluminium hydride and reoxidation afforded (&#xb1;)-abscisic acid stereospecifically. 
ER  -

