89238-99-3Relevant articles and documents
Synthesis of a chiral building block for highly functionalized polycyclic ethers
Pazos,Prez,Gndara,Gmez,Fall
, p. 7750 - 7757 (2014)
An efficient procedure for preparing enantiopure polycyclic ethers is reported. The protocol is based on the photo-oxidation/conjugate addition sequence over a chiral functionalized furan, which was prepared from commercially available tri-O-acetyl-d-gluc
Synthesis of the tricyclic core of manzamine A
Pathak, Ravindra B.,Dobson, Benjamin C.,Ghosh, Nandita,Ageel, Khalid A.,Alshawish, Madeha R.,Saruengkhanphasit, Rungroj,Coldham, Iain
, p. 3331 - 3340 (2015)
An efficient synthetic approach to the core structure of the manzamine alkaloids is reported, particularly in relation to incorporating a one-carbon unit in ring B from which the aldehyde in ircinal A or the beta-carboline unit in manzamine A could potent
Total Synthesis of DHA and DPA n-3Non-Enzymatic Oxylipins
Bultel-Poncé, Valérie,Degrange, Thomas,Durand, Thierry,Galano, Jean-Marie,Guy, Alexandre,Merad, Jérémy,Oger, Camille,Reversat, Guillaume
, (2021/12/02)
Oxylipins are formed in vivo from polyunsaturated fatty acids (PUFAs). A large structural variety of compounds is grouped under the term oxylipins, which differ from their formation mechanism (involving enzymes or not), as well as their chemical structures (cyclopentane, tetrahydrofuran, hydroxylated-PUFA, etc.). All structures of oxylipins are of great biological interest. Directly correlated to oxidative stress phenomenon, non-enzymatic oxylipins are used as systemic and/or specific biomarkers in various pathologies, and more especially, they were found to have their own biological properties. Produced in vivo as a non-separable mixture of isomers, their total synthesis is a keystone to answer biological questions. In this work, the total synthesis of three non-enzymatic oxylipins derived from docosahexaenoic acid (DHA) and docosapentanoic acid (DPAn-3) is described using a unique and convergent synthetic strategy.
Diastereoselective synthesis of trisubstituted olefins using a silicon-tether ring-closing metathesis strategy
Prunet, Jo?lle,Tiniakos, Alexander F.,Wittmann, Stéphane
, p. 2297 - 2306 (2020/04/03)
The diastereoselective synthesis of trisubstituted olefins with concomitant C-C bond formation is still a difficult challenge, and olefin metathesis reactions for the formation of such alkenes are usually not high yielding or/and diastereoselective. Herein we report an efficient and diastereoselective synthesis of trisubstituted olefins flanked by an allylic alcohol, by a silicon-tether ring-closing metathesis strategy. Both E- and Z-trisubstituted alkenes were synthesised, depending on the method employed to cleave the silicon tether. Furthermore, this methodology features a novel Peterson olefination for the synthesis of allyldimethylsilanes. These versatile intermediates were also converted into the corresponding allylchlorodimethylsilanes, which are not easily accessible in high yields by other methods.