226911-08-6Relevant articles and documents
Formal synthesis of (Z,Z)-dodeca-3,6-dien-11-olide, pheromone of oryzaephilus surinamensis and oryzaephilus mercator (Coleoptera: Cucujidae)
Vasil'ev,Serebryakov
, p. 981 - 984 (2007/10/03)
Racemic 11-Hydroxy-3(Z),6(Z)-dodecadienoic acid, the nearest precursor of the title lactone, was synthesized from 5-hydroxy-2-pentanone in eight steps with an overall yield of 1.48%. The key stage of the synthesis, regio- and stereoselective construction of the system of two conjugated Z,Z-double bonds, was accomplished by addition of two hydrogen molecules to methyl 11-oxo-2,4-dodecadien-6-ynoate in the presence of η6-(methyl benzoate)tricarbonylchromium. 1998 MAHK Hayka/Interperiodica Publishing.