151123-08-9Relevant articles and documents
Novel, Readily occurring, and Stereoselective Synthesis of Conjugated Trienes using 2-Trialkylstannyl-2,5-dihydrothiophene S,S-Dioxide
Takayama, Hiroaki,Suzuki, Takayoshi
, p. 1044 - 1045 (1988)
Conjugated trienes have been synthesized readily and stereoselectively by the coupling reaction of 2-tri-n-butylstannyl-2,5-dihydrothiophene S,S-dioxide with vinyl iodides in he presence of tetrakis(triphenylphosphine)palladium(0), followed by desulphonylation.
NOUVELLE SYNTHESE DES UNDECATRIENES-1,3,5 NATURELS
Giraudi, E.,Teisseire, P.
, p. 489 - 492 (1983)
The two natural 1,3,5-undecatrienes have been synthesized starting from pyridazine-1-oxide.The methode allows us to obtain a mixture, in which the 1,3E,5Z isomer predominates.
Two new stereoselective syntheses of (3E,5Z)-1,3,5-undecatriene
Gaudin, Jean-Marc,Morel, Cedric
, p. 5749 - 5752 (1990)
Two new and short syntheses of (3E,5Z)-1,3,5-undecatriene 1 are presented. Both approaches are based on the coupling between a C7 and a C4 synthon and afford 1 in 92-96% stereoisomeric purity.
An efficient synthesis of 1,3(E),5(Z), 1,3(E),5(E)and 1,3(Z),5(Z)-trienes: Application to the synthesis of galbanolenes and (9Z,11E)-9,11,13-tetradecatrien-1-yl acetate
Alami, Mouad,Gueugnot, Sylvie,Domingues, Elisa,Linstrumelle, Gerard
, p. 1209 - 1220 (1995)
The (Pd-Cu)-catalyzed reactions of trimethylsilyl acetylene with (E) or (Z)-chloroenynes, or 1-chloro-(1E,3E)-dienes, followed by desilylation and zinc-reduction of the triple bonds led respectively to (3E,5Z), (3Z,5Z) and (3E,5E)-trienes. Application to the syntheses of galbanolenes and (9Z,11E)-9,11,13-tetradecatrien-1-yl acetate has been realized.
Stereoselective synthesis of polyenes via Heck coupling of vinylboronate esters
Stewart, Sarah K.
, p. 3925 - 3928 (1995)
E- and Z-1-alkenyl iodides react with vinylboronate pinacol ester 1 under palladium(0) catalysed, Heck conditions to provide polyenylboronates in moderate yields after purification. The addition of either silver(I) or thallium(I) salts to the reaction mixture is essential. Alkenyl bromides are unreactive under identical reaction conditions.
Synthesis of naturally occurring diene and trienes by Te/Li exchange on (1Z,3Z)-butyltelluro-4-methoxy-1,3-butadiene
Dabdoub, Miguel J.,Dabdoub, Vania B.,Baroni, Adriano C.M.,Hurtado, Gabriela R.,Barbosa, Sandro L.
, p. 1666 - 1670 (2010)
(1Z,3Z)-Butyltelluro-4-methoxy-1,3-butadiene 2 was obtained by the hydrotelluration of (Z)-1-methoxy-but-1-en-3-ynes 1. The butadienyllithium 3 obtained by the Te/Li exchange reaction in the (1Z,3Z)-1-butyltelluro-4-methoxy-1,3-butadiene 2 reacted with aldehydes to form the corresponding alcohols 4a-d with total retention of configuration. The alcohols formed undergo hydrolysis, resulting in the α,β,γ,δ-unsaturated aldehydes of (E,E) configuration, which are precursors of trienes obtained from natural sources. The products of this reaction were employed in the synthesis of methyl-(2E,4E)-decadienoate 7, which is a component of the flavor principles of ripe Bartlett pears. Performing the Wittig reaction of the methyl triphenylphosphorane with the deca-(2E,4E)-dienal 5a, we were able to synthesize the undeca-(1,3E,5E)-triene 6a. This compound is a sex-pheromone component of the marine brown algae Fucus serratus, Dictyopteris plagiograma, and Dictyopteris australis. Performing the Wittig reaction of methyl triphenylphosphorane with the octa-(2E,4E)-dienal 5c, the nona-(1,3E,5E)-triene 6b was synthesized. The compound obtained is a sex-pheromone component of the marine brown alga Sargassum horneri. The octa-(1,3E,5E)-triene 6c was easily obtained from hepta-(2E,4E)-dienal 5d by the Wittig reaction with methyl triphenylphophorane. This compound is a sex-pheromone component of the marine brown alga Fucus serratus.
METHOD FOR PRODUCING COMPOUND HAVING CONJUGATED DIENE STRUCTURE
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Paragraph 0043, (2019/08/12)
PROBLEM TO BE SOLVED: To provide a method capable of industrially producing a conjugated diene or a conjugated triene in a short process from a raw material which is easy to obtain and handle. SOLUTION: A conjugated diene is produced from a 3-alkenal via reactions of the following first step, second step, and third step in this order: the first step of reacting a Grignard reagent with the 3-alkenal to obtain a homoallylic alcohol; a second step of reacting an esterification reagent or a halogenation reagent with the homoallylic alcohol to obtain a sulfonic ester or a halogenated product; and a third step of having a base act on the sulfinic acid ester or the halogenated product to cause an elimination reaction. SELECTED DRAWING: None COPYRIGHT: (C)2019,JPOandINPIT
An approach to the regioselective diamination of conjugated di- and trienes
Lishchynskyi, Anton,Muniz, Kilian
supporting information; experimental part, p. 2212 - 2216 (2012/03/27)
It's do or diaminate: The selective diamination of 1,3-butadienes in the presence of hypervalent iodine reagents has been developed. This oxidation process proceeds with complete selectivity in favor of diamination. Depending on the substrate, it proceeds either with 1,2- or 1,4-regioselectivity (see scheme). Copyright
A new synthetic route to 1,3,5-undecatrienes and fucoserratene
Garibyan,Ovanesyan,Makaryan,Chobanyan
, p. 455 - 458 (2008/09/20)
A new procedure for preparing natural alkatrienes, fucoserratene and 1,3,5-undecatrienes, was developed. The key step of both syntheses is stereoselective formation of double bonds by the Wittig reaction starting from (E)-4,4-dimethoxy-2-butenal.
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.
