67548-36-1Relevant academic research and scientific papers
A Modular, Enantioselective Synthesis of Resolvins D3, E1, and Hybrids
Anderson, Edward A.,Elbert, bryony L.,Llaveria, Josep,Streatfeild, penelope E.,Urbitsch, Felix
supporting information, (2020/02/28)
Resolvins D3 and E1 are important signaling molecules in the resolution of inflammation. Here, we report a convergent and flexible strategy to prepare these natural products using Hiyama-Denmark coupling of five- and six-membered cyclic alkenylsiloxanes to connect three resolvin fragments, and control the stereochemistry of the natural product (Z)-alkenes. The modular nature of this approach enables the synthesis of novel resolvin hybrids, opening up opportunities for more-extensive investigations of resolvin biology.
Pheromone synthesis. Part 257: Synthesis of methyl (2E,4Z,7Z)-2,4,7-decatrienoate and methyl (E)-2,4,5-tetradecatrienoate, the pheromone components of the male dried bean beetle, Acanthoscelides obtectus (Say)
Mori, Kenji
, p. 5589 - 5596 (2015/08/03)
Tandem Dess-Martin oxidation/Wittig reaction of (2Z,5Z)-2,5-octadien-1-ol yielded methyl (2E,4Z,7Z)-2,4,7-decatrienoate, a newly discovered pheromone component of the male dried bean beetle, while that of (±)-2,3-dodecadien-1-ol gave (±)-methyl (E)-2,4,5-tetradecatrienoate, the racemate of the known and major pheromone component. Methyl (2E,4E,7Z)-2,4,7-decatrienoate was also synthesized, which is the methyl ester of an acid metabolite of a green alga. Reduction of 2,5-octadiyn-1-ol with Zn-Cu/EtOH cleanly gave (2Z,5Z)-2,5-octadien-1-ol.
Concise stereoselective total synthesis of (+)-mueggelone
Kumar, Dachepally Aravind,Meshram, Harshadas Mitaram
, p. 1145 - 1154 (2013/03/29)
A concise synthetic route has been reported for the total synthesis of (+)-mueggelone. The syntheses of fragments were initiated from commercially available and inexpensive starting materials. The synthesis involves key steps such as Sharpless epoxidation
Enantiocontrolled synthesis of naturally occuring octadecadienoic acid derivatives, self-defensive substances against rice blast disease, by means of the Sharpless asymmetric epoxidation of unsymmetrical divinylmethanol
Honda, Toshio,Ohta, Mai,Mizutani, Hirotake
, p. 23 - 30 (2007/10/03)
(11S,121S,13S)-(9Z,15Z)- and (11R,12S,13S)-(9Z,15Z)-11-hydroxy-12,13-epoxyoctadecadienoic acids and (11R,12S,13S)-(9Z,15Z)-11,12,13-trihydroxyoctadecadienoic acid, self-defensive substances against the rice blast disease, were synthesised enantioselectively by employing the Sharpless asymmetric epoxidation reaction of the unsymmetrical divinylmethanol, as a key step.
Enantiocontrolled synthesis of (115,125,135)-(9z,15z)- and (11a,125,135)-(9z,15z)-11-hydroxy-12,13-epoxy octadecadienoic acids by means of the sharpless asymmetric epoxidation of the unsymmetrical divinylcarbinol
Honda, Toshio,Ohta, Mai,Mizutani, Hirotake
, p. 137 - 140 (2007/10/03)
(115,125,135K9Z,15Z)- and (11R,12S,13SM9Z,15Z)-11-Hydroxy-12,13-epoxy octadecadienoic acids, self defensive substances against the rice blast disease, were synthesized enantioselectively by employing the Sharpless asymmetric epoxidation reaction of the unsymmetrical divinylcarbinol, as a key step.
Synthesis of Isomeric 1,3,5,8-Undecatetraenes
Marner, Franz-Josef,Boland, Wilhelm,Jaenicke, Lothar
, p. 579 - 584 (2007/10/02)
(3E,5Z,8Z)-1,3,5,8-Undecatetraene (1a) is the smelling principle of the gametes of the brown alga Spermatochnus paradoxus.The synthesis of the isomeric 1,3,5,8-undecatetraenes 1a - c and their spectral properties are described.
