70979-88-3Relevant academic research and scientific papers
Tellurium in organic synthesis: an approach to the synthesis of (Z,E)-dienic precursors of insect pheromones
Diego, Dennis G.,Cunha, Rodrigo L.O.R.,Comasseto, Jo?o V.
, p. 7147 - 7148 (2007/10/03)
A simple and straightforward route to (Z,E)-dienic precursors of insect pheromones was developed. The route features a cross-coupling of a (Z,E)-dienic telluride with an alkyl Lipshutz cuprate.
Straightforward preparation of (2E,4Z)-2,4-heptadien-1-ol and (2E,4Z)-2,4-heptadienal
Petroski, Richard J.
, p. 3233 - 3241 (2007/10/03)
A concise synthesis of (2E,4Z)-2,4-heptadien-1-ol and (2E,4Z)-2,4-heptadienal is presented. Commercially available (Z)-2-penten-1-ol was converted to ethyl-(2E,4Z)-2,4-heptadienoate by reaction with activated MnO2 and (carboethoxymethylene)triphenylphosphorane in the presence of benzoic acid as a catalyst. Ethyl-(2E,4Z)-2,4-hep-tadienoate was converted to (2E,4Z)-2,4-heptadien-1-ol with LiAlH4. The alcohol was partially oxidized to (2E,4Z)-2,4-heptadienal with MnO2. The title compounds are male-specific, antennally active volatile compounds from the Saltcedar leaf beetle, Diorhabda elongata Brulle (Coleoptera: Chrysomelidae) and have potential use in the biological control of the invasive weed saltcedar (Tamarix spp).
The preparation and electrocyclic ring-opening of cyclobutenes: Stereocontrolled approaches to substituted conjugated dienes and trienes
Binns, Falmai,Hayes, Roy,Hodgetts, Kevin J.,Saengchantara, Suthiweth T.,Wallace, Timothy W.,Wallis, Christopher J.
, p. 3631 - 3658 (2007/10/03)
Thermal electrocyclic ring-opening of 4-alkyl-2-cyclobutene-1-carbaldehydes occurs at low temperature to give (2Z,4E)-alkadienals exclusively, and the process is exploited in transforming cis-3-cyclobutene-1,2-dimethanol 1 into a variety of naturally occurring 1,3,5-alkatrienes and 2,4-decadienoates. Desymmetrisation of 1 with Pseudomonas fluorescens lipase gives access to both enantiomers of 3-oxabicyclo[3.2.0]hept-6-en-2-one 4, for use in stereocontrolled routes to 6-oxygenated (2Z,4E)-alkadienals.
Use of cis-3-cyclobutene-1,2-dimethanol in stereoselective routes to some naturally occurring conjugated dienes and trienes
Hodgetts, Kevin J.,Saengchantara, Suthiweth T.,Wallis, Christopher J.,Wallace, Timothy W.
, p. 6321 - 6324 (2007/10/02)
Thermal electronic ring-opening of 4-alkyl-2-cyclobutene-1-carbaldehydes occurs at low temperature to give (2Z,4E)-alka-2,4-dienals exclusively, and this process is exploited en route to various isomeric naturally occurring 1,3,5-alkatrienes and 2,4-decadienoates from a single precursor, cis-3-cyclobutene-1,2-dimethanol 4.
Synthesis of 7E,9Z-dodecadienyl acetate, the sex pheromone of Lobesia botrana Shiff
Chrelashvili, Z. G.,Mavrov, M. V.,Dolidze, A. V.,Voronkov, A. P.,Serebryakov, E. P.
, p. 734 - 736 (2007/10/02)
Two syntheses of 7E,9Z-dodecadienyl acetate from 1,3-butadiyne were carried out using either 2E,4Z-heptadienyl acetate or 1-bromo-3E,5Z-octadiene as the key intermediates.The latter underwent organocopper cross-coupling with the respective complementary Grignard reagents (prepared from the corresponding 1-tert-butoxy-ω-chlorohydrins) as alkylating agents.
STEREOSELECTIVE SYNTHESIS OF (2E,4Z)-DIEN-1-OLS; KEY INTERMEDIATES FOR SYNTHESIS OF SEX PHEROMONES OF SILK WORM AND OF GRAPE VINE MOTH
Kuroda, Satoru,Katsuki, Tsutomu,Yamaguchi, Masaru
, p. 803 - 804 (2007/10/02)
Two (2E,4Z)-dien-1-ols, synthetic key intermediates for the insect pheromones with a (E,Z)-diene system, were synthesized stereoselectively by using a combination of zirconium-mediated Wittig rearrangement reaction and Peterson reaction as key steps.
STEREOSELECTIVE SYNTHESIS OF (E)-7, (Z)-9 DODECADIEN-1-YL ACETATE
Descoins, C.,Lettere, M.,Linsrumelle, G.,Michelot, D.,Ratovelomanana, V.
, p. 761 - 774 (2007/10/02)
Two convenient synthetic methods for (E)-7, (Z)-9 dodecadien-1-yl acetate, via palladium-copper catalysed reactions of acetylenic intermediates with vinylic halides, are presented.
HIGHLY STEREOCONTOROLLED SYNTHESIS OF (2E,4Z)-DIENIC ESTERS BY ALUMINA CATALYST
Tsuboi, Sadao,Masuda, Toshihide,Makino, Hiroshi,Takeda, Akira
, p. 209 - 212 (2007/10/02)
Thermal treatment of β-allenic esters (2) with alumina catalyst in aprotic solvents yielded (2E,4Z)-dienoic esters (3) in 57-87percent yields with 91-100percent stereoselectivity.
