21499-64-9Relevant articles and documents
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.
Anti-Carbometalation of Homopropargyl Alcohols and Their Higher Homologues via Non-Chelation-Controlled Syn-Carbometalation and Chelation-Controlled Isomerization
Ma, Shengming,Negishi, Ei-Ichi
, p. 784 - 785 (1997)
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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.
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.
