Readily available methyl hydrogen (R)-3-methylglutarate(2) is a useful chiral building block for the synthesis of several biologically active compounds. Enantiomerically pure (R)-2 has been employed to synthesize stereospecifically each of the two enantiomers, 1a and 1b, of 10-methyl-2-tridecanone, the sex pheromone of the southern corn rootworm, Diabrotica undecimpunctata howardi Barber. Compound (R)-2 has been also used to prepare 99% optically pure (R)-3-methyl-1-pentanol (6) and enantiomerically pure (R)-5-methyl-i-tricosyne (7). These compounds are useful building blocks suitable for the further elaboration to other chiral insect pheromones.
|Autori:||ROSSI R.; CARPITA A; CHINI M.|
|Titolo:||Synthesis of the two enantiomers of the sex pheromone of Diabrotica undecimpunctata howardi and of chiral precursors of other pheromones starting from enantiomerically pure methyl hydrogen (R)-3-methylglutarate|
|Anno del prodotto:||1985|
|Digital Object Identifier (DOI):||10.1016/S0040-4020(01)96510-X|
|Appare nelle tipologie:||1.1 Articolo in rivista|