108888-39-7Relevant articles and documents
PREMIERE SYNTHESE TOTALE DE L'ALLIODORINE. PREPARATION D'ALDEHYDES ISOPRENIQUES E A PARTIR DES METHYL-2 OXO-6 HEXENE-2 (E + Z) CARBONITRILES-1.
Tortajada, J.,Morizur, J-P.
, p. 253 - 262 (2007/10/02)
The first synthesis of alloiodorine 4EE, a constituent isolated from the duramen of a tropical tree: Cordia alliodora is reported.A mixture of E and Z isomers of 2-methyl-6-oxo-2-heptenenitrile 3 easily accesible by U.V. irradiation of 1-methyl-2-oxo-cyclopentanecarbonitrile 2 is used as starting material.E/Z isomerism is suppressed during a step of the synthesis reduction of the α,β-unsaturated nitrile function (E + Z) in the α,β-unsaturated aldehyde E ( the Z -> E isomerisation occurs during the hydrolysis of the internediate imine).The synthesis was conducted in six steps with an overall yield of 12,5percent from 1-methyl-2-oxo-cyclopentanecarbonitrile 2.