146512-85-8Relevant academic research and scientific papers
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.
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
Total synthesis of archaeal 36-membered macrocyclic diether lipid
Eguchi, Tadashi,Arakawa, Kenji,Terachi, Takumi,Kakinuma, Katsumi
, p. 1924 - 1933 (2007/10/03)
Total synthesis of archaeal 36-membered macrocyclic diether lipid 2 is reported. The synthesis is based upon stereoselective preparation of functionalized isoprenoid chains, ether-linkage formation between the isoprenoid chains with a glycerol derivative,
Optically pure acyclic bifunctional compounds from (-)-menthone. Synthesis of R-4-methyl-1-nonanol, the sex pheromone of the larger flour beetle (Tenebrio molitor L.)
Odinokov, V. N.,Ishmuratov, G. Yu.,Yakovleva, M. P.,Safiullin, R. L.,Komissarov, V. D.,Tolstikov, G. A.
, p. 1244 - 1245 (2007/10/02)
A number of novel methyl-branched chirones were prepared starting from (-)-menthone and making use of a novel, efficient, and selective oxidant, decanepersulfonic acid (DPSA).Optically pure (4R)-methyl-1-nonanol, the sex pheromone of the larger flour beetle (Tenebrio molitor L.), was synthesized.
