83541-12-2Relevant academic research and scientific papers
Ruthenium Catalysts Supported by Amino-Substituted N-Heterocyclic Carbene Ligands for Olefin Metathesis of Challenging Substrates
César, Vincent,Zhang, Yin,Ko?nik, Wioletta,Zieliński, Adam,Rajkiewicz, Adam A.,Ruamps, Mirko,Bastin, Stéphanie,Lugan, No?l,Lavigne, Guy,Grela, Karol
supporting information, p. 1950 - 1955 (2017/02/15)
N-Heterocyclic carbene (NHC) ligands IMes (Formula presented.) and IMes (Formula presented.) derived from the well-known IMes ligand by substituting the carbenic heterocycle with one and two dimethylamino groups, respectively, were employed for the synthesis of second-generation Grubbs- and Grubbs–Hoveyda-type ruthenium metathesis precatalysts. Whereas the stability of the complexes was found to depend on the degree of dimethylamino-substitution and on the type of complex, the backbone-substitution was shown to have a positive impact on their catalytic activity in ring-closing metathesis, with a more pronounced effect in the second-generation Grubbs-type series. The new complexes were successfully implemented in a number of challenging olefin metathesis reactions leading to the formation of tetra-substituted C=C double bonds and/or functionalized compounds.
Pheromone synthesis. Part 256: Synthesis of the four stereoisomers of 5,11-dimethylpentacosane, a new sex pheromone component of the male Galleria mellonella (L.), with high stereochemical purities as determined by the derivatization-HPLC analysis of the eight stereoisomers of 5,11-dimethyl-8-pentacosanol
Mori, Kenji,Akasaka, Kazuaki
, p. 4102 - 4115 (2015/06/02)
Abstract All the four stereoisomers of 5,11-dimethylpentacosane (>96.8% purity) were synthesized via the stereoisomers of 5,11-dimethyl-8-pentacosanol, whose stereoisomeric compositions could be determined precisely by their low temperature HPLC analysis after derivatization. 5,11-Dimethyl-8-pentacosanol was prepared by a Grignard reaction between 3-methylheptylmagnesium bromide and 4-methyloctadecanal, both of which were prepared from the commercially available enantiomers of citronellal (97-98% ee). Alternatively, (R)-3-methyl-1-heptanol could be prepared from methyl (R)-3-hydroxybutanoate (100% ee). Pd/C-catalyzed hydrogenation of a 5-methyl-1-alkene caused partial racemaization at C-5.
Synthesis of all the stereoisomers of 6-methyl-2-octadecanone, 14-methyl-2-octadecanone, and 6,14-dimethyl-2-octadecanone, sex pheromone components of the Lyclene dharma dharma moth, from the enantiomers of citronellal
Shikichi, Yasumasa,Mori, Kenji
, p. 1943 - 1951 (2013/01/15)
The enantiomers of citronellal were converted to all the stereoisomers of 6-methyl-2-octadecanone, 14-methyl-2-octadecanone, and 6,14-dimethyl-2- octadecanone, the female-produced sex pheromone components of the Lyclene dharma dharma moth. Three wellestablished procedures, the Wittig reaction, alkylation of alkynes, and acetoacetic ester synthesis, were employed for the carbon-carbon bond formation to connect the building blocks.
Stereoselective synthesis of (-)-PF1163A via prins cyclization
Yadav, Jhillu S.,Venkatesh,Thrimurtulu,Prasad, Attaluri R.
experimental part, p. 1255 - 1259 (2010/07/05)
A highly stereoselective and convergent total synthesis of PF1163 A is described while proving the versatility of Prins cyclization in natural product synthesis. The Prins cyclization, Yamaguchi esterification, and ring-closing metathesis reactions are th
Determination of the configuration of an Archaea membrane lipid containing cyclopentane rings by total synthesis
Montenegro, Elvira,Gabler, Bert,Paradies, Gesa,Seemann, Matthias,Helmchen, Guenter
, p. 2419 - 2421 (2007/10/03)
The fat controller: Thermoacidophilic Archaea possess membranes containing lipids consisting of mixtures of macrocyclic, 72-membered tetraethers composed of saturated isoprenoid chains linked to glycerol or higher sugars. Lipids of this type form highly s
Synthesis of the Proposed Penultimate Biosynthetic Triene Intermediate of Monensin A
Patel, Dinesh V.,VanMiddlesworth, Frank,Donaubauer, John,Gannett, Peter,Sih, Charles J.
, p. 4603 - 4614 (2007/10/02)
A convergent chiral synthesis of the putative biosynthetic triene precursor, 2b, has been accomplished.Our strategy entails the successive assembly of three key chiral synthons, prepared by enzymatic and microbial techniques.
