57981-61-0Relevant articles and documents
Nonconjugated Dienes from 1-Alkenes: Application to the Synthesis of Sex Pheromone (4E,7Z)-4,7-Tridecadienyl Acetate
Kim, Taek Hyeon,Park, Ki Man
, p. 4833 - 4836 (1995)
(4E,7Z)-4,7-Tridecadienyl acetate 1, a component of the sex pheromone was synthesized from 5-hexenyl acetate. (E)-γ,δ-Unsaturated phosphonate as the key intermediate afforded a target molecule, using the Horner-Wadsworth-Emmons (HWE) reaction and desulfonylation as the main process.
Insect pheromones and their analogs LV. Synthesis of trideca-4E,7Z-dien-1-yl acetate - Component of the sex pheromone of Phthorimaea opercucella
Odinokov,Vakhidov,Shakhmaev,Zorin
, p. 350 - 352 (2007/10/03)
Starting from propargyl alcohol and using the thermal Claisen rearrangement at the stage of constructing the (E)-double bond, we have synthesized trideca-4E, 7Z-dien-1-yl acetate - a component of the sex pheromone of the potato moth Phthorimaea opercucella (Zeller).
Stereoselective Synthesis of 1,4-Dienes. Application to the Preparation of Insect Pheromones (3Z,6Z)-Dodeca-3,6-dien-1-ol and (4E,7Z)-Trideca-4,7-dienyl Acetate
Hutzinger, Michael W.,Oehlschlager, Allan C.
, p. 4595 - 4601 (2007/10/02)
Stereoselective synthesis of Z,E- and Z,Z-1,4-dienes has been achieved by the cross-coupling of allylic substrates with vinyl organometallic reagents.Key to this strategy was the development of a method for regiospecific incorporation of a tri-n-butylstannyl group in the γ-position of the allylic cross-coupling partner.The steric bulk of this moiety ensures the stereochemical integrity of the allylic double bond throughout the coupling sequence and is easily replaced by hydrogen in the coupled product.This strategy has been applied to the synthesis of the termite trail marker pheromone 22 and the leafminer moth sex pheromone 28.