7328-34-9Relevant academic research and scientific papers
ENE REACTION OF α-THIOCARBOCATION: SIMPLE SYNTHESIS OF E,E-2,4-ALKADIENOIC ESTERS FROM 1-ALKENES
Tamura, Y.,Choi, H.-D.,Maeda, H.,Ishibashi, H.
, p. 1343 - 1344 (1981)
Pummerer reaction intermediate 2 of α-methylsulfinylacetate(1) has been found to react with 1-alkenes to afford ene adducts 3.E,E-2,4-decadienoic ester (5) was synthesized from the adduct 3 (n=5).
Iron-Catalyzed Synthesis of Sarmentine
Ignatishina, M. G.,Shakhmaev, R. N.,Zorin, V. V.
, p. 1002 - 1005 (2021/07/22)
Abstract: Stereoselective synthesis of sarmentine has been achieved via iron-catalyzed cross-coupling of pentylmagnesium bromide with ethyl (2E,4E)-5-chloropenta-2,4-dienoate obtained by one-pot oxidation–olefination of readily available (2E)-3-chloroprop
Reconstitution of a Type II Polyketide Synthase that Catalyzes Polyene Formation
Du, Danyao,Katsuyama, Yohei,Shin-ya, Kazuo,Ohnishi, Yasuo
supporting information, p. 1954 - 1957 (2018/02/10)
While type II polyketide synthases (PKSs) are known for producing aromatic compounds, a phylogenetically new subfamily of type II PKSs have been recently proposed to synthesize polyene structures. Here we report in vitro analysis of such a type II PKS, IgaPKS for ishigamide biosynthesis. The ketoreductase (Iga13) and dehydratase (Iga16) were shown to catalyze the reduction of a β-keto group and dehydration of a β-hydroxy group, respectively, to form a trans double bond. Incubation of the acyl carrier protein (Iga10), the ketosynthase/chain length factor complex (Iga11–Iga12), Iga13 and Iga16 with malonyl and hexanoyl-CoAs and NADPH followed by KOH hydrolysis resulted in the formation of four unsaturated carboxylic acids (C8, C10, C12, and C14), indicating that IgaPKS catalyzes tetraene formation by repeating the cycle of condensation, keto-reduction and dehydration with strict stereo-specificity. We propose “highly reducing type II PKS subfamily” for the polyene-producing type II PKSs.
Aggregation behavior of tetraenoic fatty acids in aqueous solution
Wang, Yonghui,Ma, Jianguo,Cheon, Hwan-Sung,Kishi, Yoshito
, p. 1333 - 1336 (2008/04/05)
(Chemical Equation Presented) Why so blue? Unique blue-shifted UV absorptions were used to follow the aggregation of C24 tetraene fatty acids in aqueous solution. Aggregation takes place through three distinct states (i.e. K→T1→T2; see picture). It is suggested that all of these aggregates are lamellar-type in a local sense but differ in the packing mode of the fatty acid backbone.
Concise preparation of the (3E,5Z)-alkadienyl system. New approach to the synthesis of principal insect sex pheromone constituents
Ragoussis, Valentine,Panopoulou, Maria,Ragoussis, Nikitas
, p. 5047 - 5051 (2007/10/03)
A new rapid and low-cost preparation of the (3E,5Z)-3,5-alkadienyl system, encountered in several insect pheromone constituents, was developed. Knoevenagel condensation of (E)-2-alkenals with ethyl hydrogen malonate in dimethyl sulfoxide, in the presence of a catalytic amount of piperidinium acetate, led to a mixture of geometrical isomers of ethyl 3,5-alkadienoates and ethyl 2,4-alkadienoates, from which the (3E,5Z)-3,5-alkadienoate was conveniently separated, by the use of urea inclusion complex formation. The importance of this procedure has been illustrated by the preparation of the (3E,5Z)-3,5-tetradecadienoic acid (megatomoic acid) 1, the (3E,5Z)-3,5- dodecadienyl acetate 2, and the (3E,5Z)-3,5-tetradecadienyl acetate 3. These compounds are the main components of insect sex pheromones and constitute synthetic targets of considerable interest for the semiochemical community.
Stereoselective synthesis of methyl and ethyl (2E,4Z)-2,4-decadienoates from (E)-4,4-dimethoxy-2-butenal
Ovanesyan,Garibyan,Badanyan
, p. 951 - 954 (2007/10/03)
Methyl and ethyl (2E,4Z)-2,4-decadienoates were synthesized starting from (E)-4,4-dimethoxy-2-butenal.
Stereo- and regiocontrolled transformations of vinyloxiranes with metal halides
Antonioletti,Bovicelli,Fazzolari,Righi
, p. 9315 - 9318 (2007/10/03)
Simple procedures for the transformation of vinyl oxiranes to trans, trans-dienes and regio- and stereocontrolled unsaturated bromohydrins are reported. (C) 2000 Elsevier Science Ltd.
Synthesis of all four isomers of (E)-4,5-dihydroxydec-2-enal using osmium-catalysed asymmetric dihydroxylation
Allevi, Pietro,Tarocco, Giorgio,Longo, Alessandra,Anastasia, Mario,Cajone, Francesco
, p. 1315 - 1325 (2007/10/03)
The enantioselective synthesis of the four possible isomers of (E)-4,5-dihydroxydec-2-enal, a cytotoxic product formed in peroxidised liver microsomal lipids, is accomplished via a Sharpless AD reaction alone or associated as appropriate with a regioselective epimerisation of one of the introduced hydroxy groups.
Expedient synthesis of unsaturated amide alkaloids from Piper spp: Exploring the scope of recent methodology
Strunz, George M.,Finlay, Heather J.
, p. 419 - 432 (2007/10/03)
The Sakai aryl aldehyde - cyclic ketone aldol - Grob fragmentation sequence was extended to cinnamaldehyde and cyclohexanone, and the product was elaborated to analogues of the alkaloid piperstachine. The effects of substituents on the reaction involving cinnamaldehyde were studied. The aldol-fragmentation sequence failed with benzaldehyde when cyclooctanone or cyclobutanone was substituted for cyclohexanone or cyclopentanone, and the reasons for this failure were examined. Four-carbon Wittig homologation of the piperonal-cyclobutanone aldol-fragmentation product, a hypothetical route to alkaloids such as retrofractamide A, was thus not viable. Instead, three-carbon homologation of the readily available piperonal-cyclopentanone product, using alkyne chemistry recently disclosed by Lu and Trost, afforded these alkaloids in excellent overall yield. The alkyne isomerization was also used to effect efficient syntheses of pellitorine and several other non-aromatic 2E,4E-dienoic Piper amide alkaloids. The Sakai aryl aldehyde - cyclic ketone aldol - Grob fragmentation sequence was extended to cinnamaldehyde and cyclohexanone, and the product was elaborated to analogues of the alkaloid piperstachine. The effects of substitutents on the reaction involving cinnamaldehyde were studied. The aldol-fragmentation sequence failed with benzaldehyde when cyclooctanone or cyclobutanone was substituted for cyclohexanone or cyclopentanone, and the reasons for this failure were examined. Four-carbon Wittig homologation of the piperonal-cyclobutanone aldol-fragmentation product, a hypothetical route to alkaloids such as retrofractamide A, was thus not viable. Instead, three-carbon homologation of the readily available piperonal-cyclopentanone product, using alkyne chemistry recently disclosed by Lu and Trost, afforded these alkaloids in excellent overall yield. The alkyne isomerization was also used to effect efficient syntheses of pellitorine and several other non-aromatic 2E,4E-dienoic Piper amide alkaloids.
A CONVENIENT STEREOSELECTIVE SYNTHESIS OF CONJUGATED DIENOIC ESTERS AND AMIDE
Ma, Dawei,Lu, Xiyan
, p. 3189 - 3198 (2007/10/02)
(2E,4E)-Dienoic esters and amides could be synthesized via the stereoselective isomerization of the corresponding 2-ynoic esters and amides, respectively, under the catalysis of ruthenium or iridium complexes.
