Synthesis of N-isobutylamide of 2e,4e-decadienoic acid(pellitorine) from butadiene-acetic acid telomer

Conclusions The N-isobutylamide of 2E,4E-decadienoic acid (pellitorine) was synthesized from 2E,7-octadien-1-yl acetate, the telomer of butadiene with acetic acid.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 11, pp. 2589–2590, November, 1982.     

A new tris-annulation reagent prepared from a butadiene telomer,and its application to steroid synthesis

Reaction of 1,7-octadien-3-one with dimethyl malonate, followed by the reduction of the ketone produced dimethyl (3-hydroxy-7-octenyl)malonate, which was converted to 9-decen-5-olide after hydrolysis and decarboxylation. Reaction of vinylmagnesium chloride with the lactone and the subsequent acylation afforded 7-acetoxy-1,11-dodecadien-3-one. This is a new tris-annulation reagent. (±)-D-homo-19-norandrosta-4-en-3-one was synthesized by using this tris-annulation reagent.     

A practical synthesis of 2,4(5)-diarylimidazoles from simple building blocks

A simple and efficient approach to selectively obtain 2,4(5)-diarylimidazoles suppressing formation of 2-aroyl-4(5)-arylimidazoles is described. The yield of each of the two products strongly depends on the reaction conditions employed. This reaction provides a simple method to prepare small libraries of biologically active compounds by parallel synthesis.     

A simple one-step synthesis of 3-amino-2,4(1H,3H)quinazolinediones

Anthranilic acids and alkyl carbazates in refluxing quinoline give high yields of 3-arnino-2,4(1H,3H)-quinazolinediones.     

Pyrolysis of sulfoxide. III. Conversion of 2-(phenylsulfinyl)enoate to 2,4-dienoate and synthesis of pellitorine

2,4-Dienoate was prepared by pyrolysis of 2-(phenylsulfinyl)enoate. N-Isobutyl-E,E-2,4-decadieneamide (pellitorine) was synthesized from decanoic acid in a satisfactory yield.     

A simple synthesis of 2,4-diaryl-1,3,5-triazines

Summary Arylamidines2 react with 5-methoxymethylen-2,2-dimethyl-1,3-dioxan-4,6-dione5 to give 2,4-diaryl-1,3,5-triazines in moderate to good yields.5 can be comprehended as a formic acid derivative which transfers a C₁-building block. Other formic acid derivatives give only poor to moderate yields of triazines by treatment with amidines. The synthetic method is applicable to aromatic amidines.

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Eine einfache Synthese von 2,4-Diaryl-1,3,5-triazinen

Zusammenfassung Die Arylamidine2 reagieren mit 5-Methoxymethylen-2,2-dimethyl-1,3-dioxan-4,6-dion5 in guten Ausbeuten zu 2,4-Diaryl-1,3,5-triazinen. Verbindung5 kann als Derivat der Ameisensäure aufgefaßt werden, welches einen C₁-Baustein überträgt. Andere Derivate der Ameisensäure ergeben bei Umsetzung mit Amidinen nur schlechte Ausbeuten an Triazinen. Die beschriebene Methode ist auf aromatische Amidine anwendbar.

     

Ene reaction of α-thiocarbocation: Simple synthesis of E,E-2,4-alkadienoic esters from 1-alkenes

Pummerer reaction intermediate $\text{2}$ of α-methylsulfinylacetate ($\text{1}$) has been found to react with 1-alkenes to afford ene adducts $\text{3}$. E,E-2,4-decadienoic ester ($\text{5}$) was synthesized from the adduct $\text{3}$ (n=5).     

A simple synthesis of octaphenylcyclotetra(siloxane)

An essential industrial monomer octaphenylcyclotetra(siloxane) or (Ph₂SiO)₄ was obtained by very simple procedures, The product was confirmed by NMR, IR, MS, elemental analysis, and X-ray crystallography.     

Synthesis of 12-acetoxy-1, 3-dodecadiene,an insect sex pheromone of the red bollworm moth,from a butadiene telomer

8-Phenoxy-1, 6-octadiene (1) formed by the Pd-catalyzed telomerization of butadiene with phonol was converted to 8-phenoxy-6-octen-1-ol (3). The alcohol 3 was converted to 8-iodo-1-phenoxy-2-octene (5). The Grignard reagent 7 prepared from 4-chloro 1-butyl tetrahydropranyl ether was coupled with the iodide 5 by the catalysis of CuI and bipyridyl to give 12-phenoxy-10-dodecen-1-ol (9), which was converted to 12-acetoxy-1-phenoxy-2-dodecene (10). Finally, 12-acetoxy-1, 3-dodecadiene (11) was obtained by the palladium catalyzed elimination of phenol from phenoxyacetoxy-dodecene (10).     

A simple synthesis of (±) 4-demethoxydaunomycinone

A new and simple synthesis of 4-demethoxy-7-deoxydaunomycinone has been carried out essentially in three steps starting from 1,4-dimethoxy-6-tetralone.     

A simple total synthesis of (±)-ascofuranone

A simple, efficient total synthesis of (±)-ascofuranone is described.     

A simple,regioselective synthesis of 1,4-bis(tert-butoxycarbonylmethyl)- tetraazacyclododecane

A convenient synthetic route to 1,4-bis(tert-butoxycarbonylmethyl)tetraazacyclododecane (cyclen) (1) with high yield and excellent regioselectivity is described. Compound 1 reacted with a range of functionalized alkyl halides under two reaction conditions to give mono-N-alkylated 1,4-bis(tert-butoxycarbonylmethyl)tetraazacyclododecane (2-9) in good yield.     

A simple,direct synthesis of Na2Fe(CO)4

Summary Reduction of anhydrous FeCl₃ in THF with sodium naphthalenide under a CO atmosphere at room temperature leads directly to Na₂Fe(CO)₄, which on reaction with alkyl bromides gives the corresponding aldehydes, ketones and carboxylic acids under appropriate conditions.     

Synthesis of (±)-dimethyl curvularin based on the palladium-catalyzed carbonylation of 3,5-dimethoxybenzyl chloride using a butadiene telomer as a building block

Palladium-catalyzed carbonylation of 3,5-dimethoxybenzyl chloride (13) with benzyl 7-hydroxyoctanoate (12) afforded benzyl 7-(3,5-dimethoxyphenylacetoxy)octanoate (6) in 70% yield, which is the precursor of Curvularin (4). The ester (12) was easily prepared from the butadiene telomer obtained by the palladium-catalyzed reaction of butadiene with acetic acid.