33081-35-5Relevant academic research and scientific papers
Diastereoselective synthesis of a lilac aldehyde isomer and its electrophysiological detection by a moth
Schneider, Marc-Andre,Doetterl, Stefan,Seifert, Karlheinz
, p. 1252 - 1259 (2013/08/15)
The monoterpene lilac aldehyde (=2-(5-ethenyl-5-methyloxolan-2-yl)propanal) is a widespread flower scent. Lilac aldehyde is emitted in high amounts from nocturnal plant species, and it is highly attractive to nocturnal moth pollinators, such as Hadena bicruris, the pollinating seed predator of Silene latifolia. Lilac aldehyde possesses three stereogenic centers and can occur in eight stereoisomers which induce different antennal responses in H. bicruris. The distribution pattern of stereoisomers differs among plant species, and if H. bicruris has different receptors for detecting different isomers, it may use these differences to discriminate flowers of S. latifolia hosts from flowers of non-host plants. To investigate the question whether the moths have in their antennae one olfactory receptor or several different receptors for the detection of the single lilac aldehyde isomers, (2S,2′S,5′S)-lilac aldehyde was diastereoselectively synthesized. (2S,2′S,5′S)-Lilac aldehyde and its isomeric mixture were tested electrophysiologically on antennae of H. bicruris. The results displayed antennal responses, which are characteristic for a single receptor that detects the different lilac aldehyde isomers. Copyright
INTRAMOLECULAR REACTIONS OF ALLYLOXY RADICALS
Johns, Amanda,Murphy, John A.,Sherburn, Michael S.
, p. 7835 - 7858 (2007/10/02)
Allyloxy radicals formed by epoxide cleavage, have cyclised onto appropriately positioned alkenes to form tetrahydrofurans, and the diastereoselectivity of the cyclisation has been studied.The reaction was used to synthesise lilac alcohols which were then used to confirm the stereochemistry of such cyclisations.
Die Cycloaddition von Allyl-Kationen an 1,3-Diene: Eine allgemeine Methode zur Synthese siebengliedriger Carbocyclen
Hoffmann, H.M.R.
, p. 29 - 48 (2007/10/02)
Allyl-Kationen reagieren mit 1,3-Dienen zu sieben-, fuenf- und sechsgliedrigen Ringen, aber auch zu Produkten der elektrophilen Substitution und zu linearen 1:1-Addukten.In diesem Beitrag werden Fortschritte auf praeparativem und mechanistischem Gebiet zusammengefasst, wobei die Synthese siebengliedriger Carbocyclen im Mittelpunkt steht.Es wird erstmals eine umfassende mechanistische Beschreibung vorgestellt: Drei Reaktionsklassen setzen den Produkttyp und die resultierende Stereochemie in Beziehung zur Nucleophilie des Diens, zur Elektrophilie des intermediaeren Allyl-Kations und zur Donorstaerke der Gruppe Y, die an das zentrale Kohlenstoffatom der Allylgruppe gebunden ist.Das Problem "Allylresonanz contra nucleophile Beteiligung von Y" wird diskutiert; experimentelle Hinweise deuten auf eine schwache Beteiligung von Y als Funktion seiner Nucleophilie.Die durch die Struktur erzwungene Planaritaet des ?-Allylsystems in Cyclopentenyl-Kationen mit gutem Donor Y fuehrt hier zu einer erhoehten Ladungstrennung und damit Elektrophilie.
A HIGHLY STEREOSELECTIVE SYNTHESIS OF DAVANONE
Bartlett, Paul A.,Holmes, Christopher P.
, p. 1365 - 1368 (2007/10/02)
Iodocyclization of the anti 4-bromobenzyl ether acetate 4f is a key step in the first stereocontrolled synthesis of the trisubstituted tetrahydrofuran davanone.
