- Exo and endohormones. XX. Synthesis of racemic 2-ethyl-1,6-dioxaspiro[4,4]nonane, the aggregation pheromone of pityogenes chalcographus (Coleoptera, Scolytidae)
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The synthesis of a diastereoisomeric mixture of 2-etyl-1,6-dioxaspiro[4,4]nonane (chalcograne) a main component of the aggregation pheromone of the spruce bark beetle Pityogenes chalcographus (Coleoptera, Scolytidae), a serious pest in European forests, by 1,7-nonanediol cyclization using Pb(OAc)4 is given below. The side products of spirocyclization were identified by GC/MS.
- Balea, Ana,Pojar-fene?an, Maria,Pop, Lidia,Oprean, Ioan,Ciupe, Hilke
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p. 465 - 469
(2007/10/03)
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- Synthesis of a Model Hapten with Cyclohexanediol and &α-Methylene-&γ-butyrolactone Groups, a Synthetic Analogue of Poison Ivy and Tulipalin Allergens Connected with a Carbon Chain
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Potential skin sensitizers 1 and 1* with two different haptenic ends, (a) a cyclohexanediol group (saturated poison ivy analogue ) and (b) an α-methylene-γ-butyrolactone moiety (tulipalin A), separated by a nine carbon atoms chain containing a double bond have been prepared.The trans, trans relationship in the substituted cyclohexanediol was secured by a tandem Michael addition-hydroboration reaction.Contrary to an earlier example of a double-headed hapten containing pyrocatechol and α-methylene-γ-butyrolactone ends, the cyclohexanediol-α-methylene-γ-butyrolactone does not show any tolerance induction to the α-methylene-γ-butyrolactone end.It therefore seems that induction of tolerance as well as sensitization requires the formation of covalent bond with a protein carrier.
- Mattes, Henri,Benezra, Claude
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p. 2732 - 2737
(2007/10/02)
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- Synthesis of codling moth attractant
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Sterospecific synthesis of an attractant for the codling moth by reacting sorbic aldehyde with an organo-metallic reagent to yield a 1-ether of trans-8-trans-10-dodecadiene-1,7-diol which is reduced via a 7-sulfonic acid ester to yield an ether of trans-8-trans-10-dodecadiene-1-ol and hydrolyzed to trans-8-trans-10-dodecadien-1-ol. SPC1
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