36237-65-7Relevant academic research and scientific papers
A short and selective synthesis of (S)-geranylcitronellol via conjugate addition of a functionalized copper reagent to 2-substituted exo-bornyl crotonates
Johansson, Anders,Olsson, Thomas,Bergstroem, Gunnar
, p. 7127 - 7128 (1996)
An asymmetric synthesis of the diterpene (S)-geranylcitronellol 1a and its acetate 1b is reported. The chirality is induced by TMSI-promoted conjugate addition of a homoallylic monoorganocopper reagent to 2-naphthyl-exo-bornylcrotonate, which proceeds wit
Identification and Composition of Clasper Scent Gland Components of the Butterfly Heliconius erato and Its Relation to Mimicry
Darragh, Kathy,Ehlers, Stephanie,H?tling, Susan,Harig, Tim,Jiggins, Chris D.,Schulz, Stefan,Stell, Matthew,Szczerbowski, Daiane
, p. 3300 - 3313 (2021/10/12)
The butterfly Heliconius erato occurs in various mimetic morphs. The male clasper scent gland releases an anti-aphrodisiac pheromone and additionally contains a complex mixture of up to 350 components, varying between individuals. In 114 samples of five different mimicry groups and their hybrids 750 different compounds were detected by gas chromatography/mass spectrometry (GC/MS). Many unknown components occurred, which were identified using their mass spectra, gas chromatography/infrared spectroscopy (GC/IR)-analyses, derivatization, and synthesis. Key compounds proved to be various esters of 3-oxohexan-1-ol and (Z)-3-hexen-1-ol with (S)-2,3-dihydrofarnesoic acid, accompanied by a large variety of other esters with longer terpene acids, fatty acids, and various alcohols. In addition, linear terpenes with up to seven uniformly connected isoprene units occur, e. g. farnesylfarnesol. A large number of the compounds have not been reported before from nature. Discriminant analyses of principal components of the gland contents showed that the iridescent mimicry group differs strongly from the other, mostly also separated, mimicry groups. Comparison with data from other species indicated that Heliconius recruits different biosynthetic pathways in a species-specific manner for semiochemical formation.
