87371-99-1Relevant academic research and scientific papers
Concise synthesis of (3 Z)-dodecen-12-olide, pheromone component of the emerald ash borer
Mayo,Silk,Magee,McConaghy
, p. 1957 - 1969 (2014/07/07)
Emerald ash borer (EAB), Agrilus planipennis Fairmaire, is an invasive insect that has killed millions of ash trees in Canada and the USA. (3Z)-Dodecen-12-olide is a known female-produced pheromone of this insect, and a concise, three-step synthesis of a
Synthesis of 3(Z)-Dodecen-12-olide - an aggregation pheromone of the flat grain beetle Crypfolestes pusillus (Coleoptera: Cucujidae)
Vasil'ev, A. A.,Engman, L.,Merkulova, V. M.
, p. 1297 - 1300 (2007/10/03)
3(Z)-Dodecen-12-olide, an aggregation pheromone of the flat grain beetle, was obtained using 1,4-cis-hydrogenation of ethyl 12-hydroxydodeca-2,4-dienoate as a key step. The dienoic ester was synthesized from 10-hydroxydec-2-enal, which, in turn, was prepa
Organoselenium-assisted route to conjugated dienoic macrolides. Synthesis of (Z)-dodec-3-en-12-olide, a pheromone of the flat grain beetle Cryptolestes pusillus (Coleoptera: Cucujidae)
Vasil'ev, Andrei A.,Engman, Lars,Serebryakov, Edward P.
, p. 611 - 615 (2007/10/03)
Oxidative elimination of the arylseleno group in (E)-2-(4-methoxyphenylseleno)dodec-4-en-12-olide gave (2Z,4E)-dodeca-2,4-diene-12-olide which on 1,4-cis-hydrogenation(η6-naphthalene)tricarbonylchromium afforded the title pheromone. (E)-2-(4-Me
Use of enyne compounds in the synthesis of insect pheromones
Ishmuratov,Ishmuratova,Odinokov,Tolstikov
, p. 25 - 30 (2007/10/03)
A new approach has been developed to the synthesis of monogenic insect pheromones with acetogenin and macrolide structures, using the low reactivity of ozone and of 9-borabicyclo[3.3.1]nonane towards an acetylenic function as compared with a vinyl function.
A concise, efficient and flexible strategy for the synthesis of the pheromones of Oryzaephilus and Cryptolesters grain beetles
Boden,Chambers,Stevens
, p. 411 - 420 (2007/10/02)
Six of the seven macrolide components of the pheromone systems of grain beetles of the genera Oryzaephilus and Cryptolestes are synthesised by new routes of greatly improved efficiency. Iterative methodology based on the Wittig olefination is employed for
Synthesis of Four Macrolide Pheromones to Define the Scope and Limitation of Enzymatic Macrolactonization
Mori, Kenji,Tomioka, Hiroki
, p. 1011 - 1018 (2007/10/02)
The macrolides, (R)-ferrulactone II (2), (Z)-3-dodecen-12-olide (3) and (5Z,13R)-5-tetradecen-13-olide (4), could be synthesized by enzymatic macrolactonization with lipases by starting from (+/-)-12, 17 and (+/-)-24, respectively.Ferrulactone I (1) was p
APPLICATION OF BIOCHEMICAL METHODS IN ENANTIOSELECTIVE SYNTHESIS OF BIOACTIVE NATURAL PRODUCTS
Mori, Kenji
, p. 393 - 406 (2007/10/02)
Enzymes as well as yeasts were used in enantioselective syntheses of bioregulators such as hormones and semiochemicals.Lipases and esterases were employed in achieving optical resolution, conversion of meso-compounds to optically active compounds, and macrolactonization.Lactase effected glucosidation of a phenolic hydroxy ketone without any protection of the functional groups.Yeasts provided a variety of optically active hydroxy esters and ketones, which served as versatile non-racemic chiral building blocks.
New Synthesis of Macrolide Pheromones of the Flat Grain Beetle, Cryptolestes pusillus Schoenherr
Sakai, Teruyuki,Hamamoto, Hiroshi,Mori, Kenji
, p. 1621 - 1628 (2007/10/02)
(Z)-3-Dodecan-12-olide 1 and (5Z,13S)-5-tetradecen-13-olide 2, the macrolide pheromones of the flat grain beetle, were synthesized by employing the acetylene zipper reaction in the key steps.
