4798-46-3Relevant academic research and scientific papers
AN ENANTIOSPECIFIC AND VERSATILE SYNTHESIS OF STATINE
Saiah, M.,Bessodes, M.,Antonakis, K.
, p. 111 - 112 (1991)
A short, enantiospecific synthesis of statine is described, starting from a readily available aldehyde.The control of chirality was effected by using the Sharpless asymmetric epoxidation procedure.
Exploiting the co-reliance of tumours upon transport of amino acids and lactate: Gln and Tyr conjugates of MCT1 inhibitors
Nair, Reji N.,Mishra, Jitendra K.,Li, Fangzheng,Tortosa, Mariola,Yang, Chunying,Doherty, Joanne R.,Cameron, Michael,Cleveland, John L.,Roush, William R.,Bannister, Thomas D.
, p. 900 - 905 (2016)
Glutamine and tyrosine-based amino acid conjugates of monocarboxylate transporter types 1 and 2 inhibitors (MCT1/2) were designed, synthesized and evaluated for their potency in blocking the proliferation of a human B lymphoma cell line that expresses the transporters Asct2, LAT1 and MCT1. Appropriate placement of an amino acid transporter recognition element was shown to augment anti-tumour efficacy vs. Raji cells. Amino acid conjugation also improves the pharmacodynamic properties of experimental MCT1/2 inhibitors.
Enantio- And Diastereoselective Construction of Contiguous Tetrasubstituted Chiral Carbons in Organocatalytic Oxadecalin Synthesis
Wada, Yuuki,Murata, Ryuichi,Fujii, Yuki,Asano, Keisuke,Matsubara, Seijiro
supporting information, p. 4710 - 4715 (2020/07/06)
The organocatalytic enantio- and diastereoselective cycloetherification of 1,3-cyclohexanedione-bearing enones involving the in situ generation of chiral cyanohydrins was developed. This transformation offers the first catalytic asymmetric approach to oxa
Access to Saturated Thiocyano-Containing Azaheterocycles via Selenide-Catalyzed Regio-A nd Stereoselective Thiocyanoaminocyclization of Alkenes
Wei, Wei,Liao, Lihao,Qin, Tian,Zhao, Xiaodan
supporting information, p. 7846 - 7850 (2019/10/10)
An efficient route for the synthesis of saturated thiocyano-containing azaheterocycles by selenide-catalyzed regio-A nd stereoselective thiocyanoaminocyclization of alkenes is disclosed. The desired products were obtained in moderate to high yields under mild conditions. The generality of this method was elucidated by its efficient application in thiocyano oxycyclization of alkenes.
Hydroxymethylation beyond Carbonylation: Enantioselective Iridium-Catalyzed Reductive Coupling of Formaldehyde with Allylic Acetates via Enantiotopic π-Facial Discrimination
Garza, Victoria J.,Krische, Michael J.
supporting information, p. 3655 - 3658 (2016/04/09)
Chiral iridium complexes modified by SEGPHOS catalyze the 2-propanol-mediated reductive coupling of branched allylic acetates 1a-1o with formaldehyde to form primary homoallylic alcohols 2a-2o with excellent control of regio- and enantioselectivity. These
Enantioselective synthesis of 3-substituted 1,2-oxazinanes via organocatalytic intramolecular aza-Michael addition
Cheng, Shuanghua,Yu, Shouyun
supporting information, p. 8607 - 8610 (2014/12/10)
A highly enantioselective intramolecular 6-exo-trig aza-Michael addition was developed to afford chiral 3-substituted 1,2-oxazinanes in high yields (up to 99% yield) and good enantioselectivities (up to 98/2 er). These reactions were enabled by a quinine-derived primary-tertiary diamine as a catalyst and pentafluoropropionic acid (PFP) as a co-catalyst.
Grubbs cross-metathesis pathway for a scalable synthesis of γ-keto-α,β-unsaturated esters
Nair, Reji N.,Bannister, Thomas D.
, p. 1467 - 1472 (2014/03/21)
A direct and scalable route to γ-keto-α,β-unsaturated esters, useful intermediates in medicinal chemistry and natural products synthesis, is reported. The key step involves the use of Grubbs' second-generation olefin metathesis catalyst for cross-metathes
Modular preparation of diverse dipyrrolemethanes
Pham, Cindy C.,Park, Michelle H.,Pham, Jenny Y.,Martin, Sadie G.,Schramm, Michael P.
, p. 1165 - 1173 (2013/06/05)
A modular synthesis of polyfunctional dipyrrolemethanes is presented. Diverse side chains are introduced to 2-carboxypyrrole building blocks in two to four steps, resulting in a collection of substituted pyrroles that, when condensed in one step, give ris
Stereoselective synthesis of functionalized cyclic amino acid derivatives via a [2,3]-stevens rearrangement and ring-closing metathesis
Nash, Aaron,Soheili, Arash,Tambar, Uttam K.
supporting information, p. 4770 - 4773 (2013/10/08)
Unnatural cyclic amino acids are valuable tools in biomedical research and drug discovery. A two-step stereoselective strategy for converting simple glycine-derived aminoesters into unnatural cyclic amino acid derivatives has been developed. The process includes a palladium-catalyzed tandem allylic amination/[2,3]-Stevens rearrangement followed by a ruthenium-catalyzed ring-closing metathesis. The [2,3]-rearrangement proceeds with high diastereoselectivity through an exo transition state. Oppolzer's chiral auxiliary was utilized to access an enantiopure cyclic amino acid by this approach, which will enable future biological applications.
Highly efficient kinetic resolution of allylic alcohols with terminal double bond
Marques, Francisco A.,Oliveira, Marcos A.,Frensch, Gustavo,Sales Maia, Beatriz Helena L. N.,Barison, Andersson,Lenz, Cesar A.,Guerrero Jr., Palimecio G.
experimental part, p. 696 - 700 (2012/06/04)
In this study, the lipase-catalyzed kinetic resolution (Novozyme 435) was employed to prepare chiral allylic alcohols and acetates with terminal double bonds in enantiomeric excesses ranging from 94 to >99 %.
