160349-52-0Relevant academic research and scientific papers
On the Asymmetric Induction in Proline-Catalyzed Aldol Reactions: Reagent-Controlled Addition Reactions of 2,2-Dimethyl-1,3-dioxane-5-one to Acyclic Chiral α-Branched Aldehydes
Marjanovic Trajkovic, Jasna,Milanovic, Vesna,Ferjancic, Zorana,Saicic, Radomir N.
, p. 6146 - 6153 (2017/11/15)
Reagent stereocontrol in the proline-catalyzed aldol reaction of 2,2-dimethyl-1,3-dioxane-5-one 1 with chiral aldehydes has been investigated. Synthetically useful levels of diastereoselectivity could be achieved in reactions with acyclic chiral α-oxy and α-amino aldehydes in both matched and mismatched cases. By using this reaction as a key step, two medicinally relevant azasugars, 1-deoxy-galactonojirimycin (9) and 2,5-dideoxy-2,5-imino-d-altritol (10), were efficiently synthesized.
Stereoselective allylation reactions of acyclic and chiral α-amino-β-hydroxy aldehydes
Myeong, In-Soo,Lee, Yong-Taek,Lee, Sang-Hyun,Jung, Changyoung,Kim, Jin-Seok,Park, Seok-Hwi,Kang, Jihun,Lee, Seung-Jong,Ye, In-Hae,Ham, Won-Hun
supporting information, p. 1053 - 1060 (2017/10/05)
Stereoselective allylation reactions of acyclic and chiral α-amino-β-hydroxy aldehydes affording chiral β-amino-α,γ-diols are described. Several Lewis acids (BF3·OEt2, SnCl4, TiCl4, ZnCl2, and MgBr2·OEt2) were employed to mediate the allylation reactions. The reactions of anti-α-NHCbz-β-OTBS substrates mediated by SnCl4 afforded syn-selective products. The same reaction conditions also gave satisfactory results for the reactions of syn-α-NHCbz-β-OTBS substrates. The mechanism involves α-chelation between the amido group and aldehyde oxygen.
C-Functionalized chiral dioxocyclam and cyclam derivatives with 1,2,3-triazole units: Synthesis, complexation properties and crystal structures of copper(ii) complexes
Felten,Petry,Henry,Pellegrini-Mo?se,Selmeczi
, p. 1507 - 1520 (2016/02/20)
New C-functionalized syn- and anti-dioxocyclam and cyclam derivatives with 1,2,3-triazole units attached to carbon atoms within the skeleton were designed as valuable bifunctional chelating agents for applications in nuclear medicine. These macrocyclic chelators were prepared via a multi-step sequence involving α- and β-amino acids, and their copper(ii) complexation properties were evaluated. A solution structure in which the triazoles are in axially coordinating positions was proposed for the [Cu(anti-27)]2+ complex. Promising results have been obtained regarding the complexation kinetics (1/2 = 3.21 d, 5 M HCl, 50°C).
Total synthesis of a piperidine alkaloid, microcosamine A
Raji Reddy, Chada,Latha, Bellamkonda,Warudikar, Kamalkishor,Singarapu, Kiran Kumar
, p. 251 - 258 (2015/12/30)
The first asymmetric total synthesis of a new natural piperidine alkaloid, microcosamine A, has been accomplished from d-serine and d-methyl lactate as chiral pool starting materials. Key features of the strategy include the utility of Horner-Wadsworth-Emmons reaction, Luche reduction, intramolecular carbamate N-alkylation to form the piperidine framework and Julia-Kocienski olefination to install the triene side-chain.
Biomimetic total synthesis and antimicrobial evaluation of anachelin H
Gademann, Karl,Bethuel, Yann,Locher, Hans H.,Hubschwerlen, Christian
, p. 8361 - 8370 (2008/09/18)
(Chemical Equation Presented) The first biomimetic total synthesis of the iron chelator anachelin H isolated from the cyanobacterium Anabaena cylindrica is reported. A first generation approach delivered one enantiomeric series of the polyketide fragment. Comparison of the 1H NMR data suggested the relative configuration of this anachelin fragment. The relative and absolute configuration of anachelin H was then established by total synthesis. A second generation approach involved the enzymatic conversion of N,N-dimethyltyramine to the anachelin chromophore. It was demonstrated that the enzyme tyrosinase is activated by the product during this reaction, the anachelin chromophore can serve as a tyrosinase activator. Anachelin H was evaluated against a panel of eleven bacterial and fungal pathogens, and moderate antibiotic activity (32 μg/mL) against Moraxella catarrhalis was found.
Reduction of peptide character of HIV protease inhibitors that exhibit nanomolar potency against multidrug resistant HIV-1 strains
Tamamura, Hirokazu,Koh, Yasuhiro,Ueda, Satoshi,Sasaki, Yoshikazu,Yamasaki, Tomonori,Aoki, Manabu,Maeda, Kenji,Watai, Yoriko,Arikuni, Hisashi,Otaka, Akira,Mitsuya, Hiroaki,Fujii, Nobutaka
, p. 1764 - 1768 (2007/10/03)
Novel HIV protease inhibitors containing a hydroxyethylamine dipeptide isostere as a transition state-mimic king structure were synthesized by combining substructures of known HIV protease inhibitors. Among them, TYA5 and TYB5 were proven to be not only p
