244252-53-7Relevant academic research and scientific papers
Short synthesis of labeled and unlabeled 6Z,9Z,12Z,15-hexadecatetraenoic acid as metabolic probes for biosynthetic studies on diatoms
Pohnert, Georg,Adolph, Sven,Wichard, Thomas
, p. 159 - 166 (2004)
We describe a short synthesis of the unusual polyunsaturated 6Z,9Z,12Z,15-hexadecatetraenoic acid found in marine and fresh water diatoms. Using a one pot reductive bis-Wittig-olefination, the homoconjugated tetraene backbone of the fatty acid can be gene
(6Z,9Z,12Z)-6,9,12-Octadecatriene and (3Z,6Z,9Z,12Z)-3,6,9,12-icosatetraene, the novel sex pheromones produced by emerald moths
Yamakawa, Rei,Do, Nguyen Duc,Adachi, Yasushi,Kinjo, Masakatsu,Ando, Tetsu
, p. 4738 - 4740 (2011/03/21)
(6Z,9Z,12Z)-6,9,12-Octadecatriene and (3Z,6Z,9Z,12Z)-3,6,9,12-icosatetraene, hydrocarbons unsaturated more highly than usual lepidopteran Type II pheromones, were identified from geometrid females of Hemithea tritonaria and Thalassodes immissaria intaminata, respectively. The triene was synthesized by a double Wittig reaction between hexanal and an ylide derived from (Z)-1,6-diiodo-3-hexene, and the tetraene was synthesized by a coupling between (Z)-3-undecenal and an ylide derived from (3Z,6Z)-1-iodo-3,6-nonadiene. Each synthetic compound attracted males of the corresponding emerald moths in a field.
Highly efficient one-pot double-Wittig approach to unsymmetrical (1Z,4Z,7Z)-homoconjugated trienes
Pohnert, Georg,Boland, Wilhelm
, p. 1821 - 1826 (2007/10/03)
We describe a novel one-pot double-Wittig approach towards unsymmetrically substituted skipped trienes using the symmetrical (Z)-hex-3- ene-1,6-bis(triphenylphosphonium iodide) (2) as key reagent. Double alkenylation of the corresponding bis(ylide) 3 with sequentially added aldehydes gives (Z)-1,4,7-homoconjugated trienes in good yields. Dissymmetrization of the bis(ylide) 3 is feasible, since it displays enhanced reactivity compared to the monoylide resulting from the first olefination. Symmetrical products from statistical coupling of the bis(ylide) 3 can be drastically suppressed by slow release of the first aldehyde component through in situ thermal decomposition of an intermediate aluminate complex, generated by reduction of a methyl ester with DIBAL-H. The novel strategy is successfully applied to the one-pot synthesis of functionalized and isotopically labelled polyunsaturated fatty acids as well as to the synthesis of the geometrid moth pheromone (3Z,6Z,9Z)-nonadeca-1,3,6,9-tetraene (6a). The dissymmetrization strategy was also found to be suitable for the synthesis of homoconjugated dienes from 1,3-propylbis(triphenylphosphonium bromide).
Synthesis of volicitin: A novel three-component Wittig approach to chiral 17-hydroxylinolenic acid
Pohnert, Georg,Koch, Thomas,Boland, Wilhelm
, p. 1087 - 1088 (2007/10/03)
A short stereoselective synthesis of both enantiomers of N-(17-hydroxylinolenoyl)-L-glutamine (volicitin) 12, an elicitor of plant volatile biosynthesis from beet armyworm salivary secretion, is described; the protected 17-hydroxylinolenic acid 4 moiety o
