16066-84-5Relevant articles and documents
A practical approach to the synthesis of 14C-labeled amino acid and simple peptide
Ekhato,Huang
, p. 107 - 115 (1994)
A convenient method for the synthesis of phenylmethyl N-methyl[carboxy-14C]glycine hydrochloride (7) is described. It involves the carboxylation of transmetalated organostannane compound 4 which itself is accessible by established procedure. Success in preparing the labelled amino acid Z enabled us to synthesize target N-glycyl-N-methyl[carboxy-14C]glycine (10) by conventional coupling protocol.
Studies on the Synthesis of the Alkaloid (-)-Gilbertine via Indolidene Chemistry
Feldman, Ken S.,Folda, Tamara S.
, p. 4566 - 4575 (2016)
A synthesis route to the pentacyclic alkaloid (-)-gilbertine, which features a cyclization cascade passing through a transient indolidene intermediate, was pursued. A key stereochemical relationship was set via a Nicholas-type enolate alkylation. Ultimately, undesired C-N cyclization thwarted the final projected C-C bond forming ring closure, and gilbertine could not be prepared by this route.
Synthesis and Evaluation of PPARδAgonists That Promote Osteogenesis in a Human Mesenchymal Stem Cell Culture and in a Mouse Model of Human Osteoporosis
Kress, Brian J.,Kim, Dong Hyun,Mayo, Jared R.,Farris, Jeffery T.,Heck, Benjamin,Sarver, Jeffrey G.,Andy, Divya,Trendel, Jill A.,Heck, Bruce E.,Erhardt, Paul W.
, p. 6996 - 7032 (2021/05/29)
We synthesized a directed library of compounds to explore the structure-activity relationships of peroxisome proliferator-activated receptor δ(PPARδ) activation relative to mesenchymal stem cell (MSC) osteogenesis. Our scaffold used para-substituted cinnamic acids as a polar headgroup, a heteroatom and heterocycle core connecting units, and substituted phenyl groups for the lipophilic tail. Compounds were screened for their ability to increase osteogenesis in MSCs, and the most promising were examined for subunit specificity using a quantitative PPAR transactivation assay. Six compounds were selected for in vivo studies in an ovariectomized mouse model of human postmenopausal osteoporosis. Four compounds improved bone density in vivo, with two (12d and 31a) having activity comparable to that of GW0742, a well-studied PPARδ-selective agonist. 31a (2-methyl-4-[N-methyl-N-[5-methylene-4-methyl-2-[4-(trifluoromethyl)phenyl]thiazole]]aminocinnamic acid) had the highest selectivity for PPARδcompared to other subtypes, its selectivity far exceeding that of GW0742. Our results confirm that PPARδis a new drug target for possible treatment of osteoporosis via in situ manipulation of MSCs.
Catalyst-Free Decarboxylation of Carboxylic Acids and Deoxygenation of Alcohols by Electro-Induced Radical Formation
Chen, Xiaoping,Luo, Xiaosheng,Peng, Xiao,Guo, Jiaojiao,Zai, Jiantao,Wang, Ping
supporting information, p. 3226 - 3230 (2020/02/27)
Electro-induced reduction of redox active esters and N-phthalimidoyl oxalates derived from naturally abundant carboxylic acids and alcohols provides a sustainable and inexpensive approach to radical formation via undivided electrochemical cells. The resulting radicals are trapped by an electron-poor olefin or hydrogen atom source to furnish the Giese reaction or reductive decarboxylation products, respectively. A broad range of carboxylic acid (1°, 2°, and 3°) and alcohol (2° and 3°) derivatives are applicable in this catalyst-free reaction, which tolerated a diverse range of functional groups. This method features simple operation, is a sustainable platform, and has broad application.
A Redox Strategy for Light-Driven, Out-of-Equilibrium Isomerizations and Application to Catalytic C-C Bond Cleavage Reactions
Ota, Eisuke,Wang, Huaiju,Frye, Nils Lennart,Knowles, Robert R.
supporting information, p. 1457 - 1462 (2019/01/25)
We report a general protocol for the light-driven isomerization of cyclic aliphatic alcohols to linear carbonyl compounds. These reactions proceed via proton-coupled electron-transfer activation of alcohol O-H bonds followed by subsequent C-C β-scission of the resulting alkoxy radical intermediates. In many cases, these redox-neutral isomerizations proceed in opposition to a significant energetic gradient, yielding products that are less thermodynamically stable than the starting materials. A mechanism is presented to rationalize this out-of-equilibrium behavior that may serve as a model for the design of other contrathermodynamic transformations driven by excited-state redox events.
Stereoselective preparation of (1Z)- and (1E)-N-Boc-1-amino-1,3-dienes by stereospecific base-promoted 1,4-elimination
Tayama, Eiji,Toma, Yuka
supporting information, p. 554 - 559 (2015/02/18)
The base-promoted 1,4-elimination reaction of N-Boc-1-amino-4-methoxy-2-alkene 1 is shown to proceed with perfect stereoselectivity to afford the corresponding N-Boc-1-amino-1,3-diene 2 in good yields. The reaction is highly stereospecific. The substrate
Palladium-catalyzed γ-selective arylation of zincated Boc-allylamines
Millet, Anthony,Baudoin, Olivier
supporting information, p. 3998 - 4000 (2014/08/18)
The regio- and diastereoselective arylation of Boc-protected allylamines was performed via a one-pot lithiation/transmetalation to zinc/cross-coupling sequence, through an appropriate choice of a phosphine ligand. A variety of γ-arylated products were obtained in moderate to good yield, and the products could be directly transformed into valuable γ-arylamines and β-aryl aldehydes.
Copper(II)-acid catalyzed cyclopropanation of 1,3-dienamides by electrophilic activation of α-aryl diazoesters
Tayama, Eiji,Horikawa, Kouki,Iwamoto, Hajime,Hasegawa, Eietsu
supporting information, p. 3041 - 3044 (2014/05/20)
Copper(II)-acid catalyzed cyclopropanation of electron-rich alkenes, such as 1,3-dienamides, with α-aryl diazoesters are described. The reaction could be performed without rare metal catalysts, excess substrate, or the need for the slow addition of the diazoesters.
On the synthesis of α-amino sulfoxides
Rayner, Peter J.,Gelardi, Giacomo,O'Brien, Peter,Horan, Richard A. J.,Blakemore, David C.
, p. 3499 - 3512 (2014/05/20)
A synthetic study on the preparation of N-Boc α-amino sulfoxides has revealed an unexpected instability which is believed to be due to α-elimination of the sulfoxide to give an iminium ion. Full synthetic details are reported on two main synthetic routes: lithiation and sulfinate trapping of N-Boc heterocycles and oxidation of N-Boc α-amino sulfides. Six novel α-amino sulfoxides were successfully prepared and isolated. It is speculated that four other α-amino sulfoxides were synthesised but could not be isolated due to their propensity to α-eliminate the sulfoxide. Ultimately, a stable, cyclic N-Boc α-amino sulfoxide was prepared and this successful synthesis relied on the α-amino sulfoxide being part of a bicyclic [3.1.0] fused ring system that could not undergo α-elimination of the sulfoxide. the Partner Organisations 2014.
A mild and green method for the N-BOC protection of amines without assistant of catalyst under solvent-free conditions
Mojtahedi, Mohammad Majid,Niknejad, Nina,Veisi, Hojat
, p. 121 - 125 (2013/07/26)
A facile, green and versatile method for the Boc protection of amines has been developed by a treatment with (Boc)2O without any additive at room temperature. The method is general for the preparation of N-Boc derivatives of aliphatic (acyclic and cyclic), aromatic, and heteroaromatic amines; primary and secondary amines. The advantages of this method are green, simplicity, short reaction times and excellent yields.
