84237-05-8Relevant 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 a comprehensive polyprenol library for the evaluation of bacterial enzyme lipid substrate specificity
Wu, Baolin,Woodward, Robert,Wen, Liuqing,Wang, Xuan,Zhao, Guohui,Wang, Peng George
, p. 8162 - 8173 (2014/01/06)
Polyprenols, a universal class of glycan-carrier lipids, play important roles in glycan biosynthesis in wide variety of living organisms. The chemical synthesis of natural polyisoprenols such as undecaprenol and dolichols, and even more so the synthesis o
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.
A concise stereoselective formal total synthesis of the cytotoxic macrolide (+)-Neopeltolide via Prins cyclization
Yadav, Jhillu Singh,Krishana, Gunda Gopala,Kumar, Satya Narayana
experimental part, p. 480 - 487 (2010/03/03)
A convergent and highly stereoselective formal total synthesis of the naturally occurring, cytotoxic 14-membered macrolide neopeltolide has been achieved via two Prins cyclizations.
Total synthesis of an antitubercular lactone antibiotic, (+)-tubelactomicin A
Hosokawa, Seijiro,Seki, Masashi,Fukuda, Hisato,Tatsuta, Kuniaki
, p. 2439 - 2442 (2007/10/03)
(+)-Tubelactomicin A (1), an antitubercular lactone, has been synthesized from (S)-citronellol (2) and 2-deoxy-l-ribonolactone (18) through intramolecular Diels-Alder reaction, Suzuki-Miyaura coupling, and Shiina macrolactonization.
Synthetic studies toward potent cytotoxic agent amphidinolide B: Synthesis of the C8-C18 fragment
Chakraborty,Thippeswamy
, p. 150 - 152 (2007/10/03)
A practical synthesis of the C8-C18 fragment 1 of amphidinolide B is described in which the Stille coupling method was employed to construct the trisubstituted C28=C13-C14=C15 's-cis-1,3-diene' moiety from suitably functionalized vinyl iodide (4) and vinyl stannane (5) fragments, the former being prepared from an acetylene precursor using Negishi's carboalumination/iodination method.
A practical synthesis of 3(S)-methyl-heptanoic acid from (S)-citronellol
Breitenbach, Ralph,Chiu, Charles K.-F.,Massett, Stephen S.,Meltz, Morgan,Murtiashaw, C. William,Pezzullo, Susan L.,Staigers, Thomas
, p. 435 - 442 (2007/10/03)
Chiral 3-methyl-heptanoic acid is readily accessible by functional group manipulation of optically active citronellol. In principle, this approach is general and could be applied to the synthesis of chiral 3-methyl-alkanoic acids seven carbon atoms in length and longer.
Pheromone Synthesis, CLXVII. - Synthesis of All of the Eight Stereoisomers of Methyl 2,6,10-Trimethyltridecanoate, the Male-produced Pheromone of the Stink Bugs, Euschistus heros and E. obscurus
Mori, Kenji,Murata, Noriaki
, p. 1153 - 1160 (2007/10/02)
All of the eight possible stereoisomers of methyl 2,6,10-trimethyltridecanoate (1), the male-produced attractant pheromone of the South American soybean pest, Euschistus heros, and that of E. obscurus, are synthesized by starting from the enantiomers of citronellol (2) and methyl 3-hydroxy-2-methylpropanoate (9). - Key Words: Euschistus heros / Euschistus obscurus / Pheromones / Stink bugs / Sulfones, alkylation of / Tridecanoate, methyl 2,6,10-trimethyl-
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.
