21499-64-9Relevant academic research and scientific papers
The synthesis of d6-α-Farnesene
Fielder,Rowan
, p. 1075 - 1085 (1994)
d6-α-Farnesene (3,7-dimethyl-11-2H3-methyl-12,12,12-2H3-dodeca-1,3E,6E,10 -tetraene) has been synthesised by two routes. Thermolysis of 2-geranyl-3-methylsulpholene (5) yielded unlabelled α-famesene (93%) which was epoxidized at Δ10 in 31% yield. Oxidative cleavage of the epoxide (42%) and Wittig elaboration of the resultant trienal with d6-isopropyl triphenylphosphorane gave d6-α-farnesene (73%). Alternatively, selective epoxidation of (5) gave the terminal 6',7' mono-epoxide in 74% yield. Oxidative cleavage (73%) and Wittig elaboration of the resultant aldehyde yielded deuterated 2-geranyl-3-methylsulpholene (46%). Thermal elimination of sulphur dioxide afforded the title compound in 91% yield.
Behaviorally active green leaf volatiles for monitoring the leaf beetle, Diorhabda elongata, a biocontrol agent of saltcedar, Tamarix spp.
Cosse, Allard A.,Bartelt, Robert J.,Zilkowski, Bruce W.,Bean, Daniel W.,Andress, Earl R.
, p. 2695 - 2708 (2006)
Biological activity and chemistry of host plant volatiles were investigated for Diorhabda elongata, Brulle (Coleoptera: Chrysomelidae), a biological control agent for the invasive tree, saltcedar (Tamarix spp., Tamaricaceae). Gas chromatographic-electroantennographic detection (GC-EAD) analysis of volatiles collected from adult D. elongata feeding on saltcedar foliage or from saltcedar foliage alone showed 15 antennally active compounds. These compounds were more abundant in collections from beetle-infested foliage. Antennally active compounds were identified by GC-mass spectrometry (MS) and confirmed with authentic standards. The emissions of the most abundant GC-EAD-active compounds, green leaf volatiles (GLV), were quantitated by GC-MS. A blend of four GLV compounds, mimicking the natural blend ratio, was highly attractive to male and female D. elongata in the field, and a combination of GLV and male-produced aggregation pheromone attracted significantly greater numbers of D. elongata than did either bait alone. A preliminary experiment with a blend of seven additional GC-EAD-active saltcedar volatiles did not show any behavioral activity. The combination of the pheromone and the green leaf odor blend could be a useful attractant in detecting the presence of the biocontrol agent, D. elongata, in stands of saltcedar newly colonized by the beetle.
PROCESS FOR MAKING A CONJUGATED DIENE FROM AN ALLYL ALCOHOL
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Page/Page column 36, (2022/01/05)
An in-situ method for making a conjugated diene from an allyl alcohol comprising the conversion of the allyl alcohol to an allyl carbonate, allyl ester or allyl formate with concomitant or subsequent conversion of the allyl carbonate, allyl ester or allyl formate to the conjugated diene; the products obtained by said method, and the uses of said products.
Enantioselective Conversion of Oligoprenol Derivatives to Macrocycles in the Germacrene, Cembrene, and 18-Membered Cyclic Sesterterpene Series
Reddy, D. Srinivas,Corey
supporting information, p. 16909 - 16913 (2018/12/14)
A new enantio-and diastereoselective process has been developed for the efficient conversion of farnesol and other oligoprenyl alcohols to chiral 10-, 14-, and 18-membered cyclization products, including germacrenol, (+)-costunolide, 3-β-elemol, and epi-mukulol. The key cyclization reaction utilizes ω-bromo aldehyde substrates, a chiral ligand, and indium powder as the reagent at -78 °C and generates 10-, 14-, and 18-membered cyclic products in 70-74% yield and 94-95% ee.
A general and efficient method for the palladium-catalysed conversion of allylic alcohols into their corresponding dienes
Ostrowski, Karoline A.,Vogelsang, Dennis,Vorholt, Andreas J.
, p. 1302 - 1305 (2016/03/09)
A general method was established, converting a broad range of allylic alcohols directly and quantitatively into their corresponding dienes. The developed protocol allows the direct use of allylic alcohols, circumventing the need for their derivatisation into more reactive precursors, thereby minimising waste production with water as the sole co-product.
Revisiting the Male-Produced Aggregation Pheromone of the Lesser Mealworm, Alphitobius diaperinus (Coleoptera, Tenebrionidae): Identification of a Six-Component Pheromone from a Brazilian Population
Hassemer, Marla J.,Sant'Ana, Josué,Borges, Miguel,Withall, David,Pickett, John A.,De Oliveira, Márcio W.M.,Laumann, Raul A.,Birkett, Michael A.,Blassioli-Moraes, Maria C.
, p. 6809 - 6818 (2016/09/23)
The lesser mealworm, Alphitobius diaperinus Panzer 1797 (Coleoptera: Tenebrionidae), is a cosmopolitan insect pest affecting poultry production. Due to its cryptic behavior, insecticide control is usually not efficient. Thus, sustainable and effective methods would have an enormous and positive impact in poultry production. The aim of this study was to confirm the identity of the male-produced aggregation pheromone for a Brazilian population of A. diaperinus and to evaluate its biological activity in behavioral assays. Six male-specific compounds were identified: (R)-limonene (1), (E)-ocimene (2), 2-nonanone (3), (S)-linalool (4), (R)-daucene (5), all described before in an American population, and a sixth component, (E,E)-α-farnesene (6), which is apparently exclusive to a Brazilian population. Y-Tube bioassays confirmed the presence of a male-produced aggregation pheromone and showed that all components need to be present in a similar ratio and concentration as emitted by male A. diaperinus to produce a positive chemotactic response.
Templating effects in aristolochene synthase catalysis: Elimination versus cyclisation
Faraldos, Juan A.,Gonzalez, Veronica,Senske, Michael,Allemann, Rudolf K.
supporting information; experimental part, p. 6920 - 6923 (2011/11/04)
Analysis of the products generated by mutants of aristolochene synthase from P. roqueforti (PR-AS) revealed the prominent structural role played by the aliphatic residue Leu 108 in maintaining the productive conformation of farnesyl diphosphate to ensure C1-C10 (σ-bond) ring-closure and hence (+)-aristolochene production.
Highly regio- and stereoselective synthesis of (Z)-trisubstituted alkenes via propyne bromoboration and tandem Pd-catalyzed cross-coupling
Wang, Chao,Tobrman, Tomas,Xu, Zhaoqing,Negishi, Ei-Ichi
supporting information; experimental part, p. 4092 - 4095 (2009/12/06)
Contrary to all previous reports, bromoboration of propyne with BBr 3 proceeds in ≥98% syn-selectivity to produce (Z)-2-bromo- 1propenyldibromoborane (1). Although 1 Is readily prone to stereoisomerization, It can be converted to the pinacolboronate (2) of ≥ 98% isomeric purity by treatment with pinacol. which may then be subjected to Negishi coupling to give tri substituted (2)-alkenylpinacolboronates (3) containing various R groups In 73-90% yields. Iodinolysis of 3 affords alkenyl iodides (4) In 80-90% yields. All alkenes isolated and identified are ≥98% Z.
Sesquiterpenes produced by truncated taxadiene synthase
Huang,Williams,Roessner,Scott
, p. 9701 - 9704 (2007/10/03)
Soluble, highly active N-terminal truncated taxadiene synthase catalyzes the formation of an isomeric mixture of taxadienes from geranylgeranyl diphosphate. Farnesyl diphosphate was also found to be a good substrate, producing four sesquiterpenes which were characterized. The dual activities of taxadiene synthase and product inhibition caused by sesquiterpene metabolites make it imperative that active GGDP synthase be present in order for multi-enzyme systems to follow the taxol pathway in vitro. (C) 2000 Published by Elsevier Science Ltd.
Characterization of vinyl-substituted, carbon-carbon double bonds by GC/FT-IR analysis.
Svatos,Attygalle
, p. 1827 - 1836 (2007/10/03)
Vapor-phase infrared spectra allow the determination of the stereochemistry of carbon-carbon double bonds conjugated with a vinyl group. Cis and trans isomers of unsubstituted 1,3-alkadienes can be differentiated on the basis of the differences observed in the 900-1000 cm-1 region (spectra of cis isomers show two bands at 993 and 906 cm-1, while those of trans compounds show three absorptions at 998, 949, and 902 cm-1) and the 1590-1650 cm-1 region (the C=C stretch bands are observed at 1595 and 1642 cm-1 for cis compounds and at 1604 and 1650 cm-1 for trans compounds). Compounds bearing CH2=CHC(CH3)=CHCH2- and CH2=CHC(=CH2)-CH2- structural moieties, referred to as alpha- and beta-type compounds, are frequently encountered as natural products. For compounds bearing alpha-type groups, the cis/trans configuration of the trisubstituted double bond can be determined unambiguously. An absorption at 3095-3091 cm-1, for the =CH2 stretch vibration, is common to both of these groups; however, due to the presence of two =CH2 groups, the relative intensity of the band is much higher for beta-type compounds. For alpha-type compounds, a cis configuration at the C-3 carbon atom is characterized by a =CH2 wag absorption at 907-906 cm-1. For beta-type compounds and 3E-alpha-type compounds, this band appears at 899-897 cm-1. In addition, a wavy "fingerprint" pattern with two minima at 1632 (low intensity) and 1595-1594 cm-1 (high intensity) is characteristic for beta-type compounds. Our generalizations are based on spectra of cis and trans ocimene, myrcene, and dehydration products of many 3-methyl-1-alken-3-ols. Six isomers of farnesene can be characterized by GC/FT-IR. Furthermore, gas-phase IR allows the determination of the configuration of the trisubstituted double bond at C-3 in alpha-type farnesene congeners. For example, the homo- and bishomofarnesene isomers from Myrmica ants were shown to include a 3Z bond.
