169139-89-3Relevant academic research and scientific papers
A new enantioselective approach to the core structure of hypoxia selective prodrugs related to the duocarmycins
Heinrich, Daniel M.,Youte, Jean-Jacques,Denny, William A.,Tercel, Moana
, p. 7000 - 7003 (2012/02/05)
The indoline scaffold of hypoxia selective prodrugs of DNA-alkylating agents related to the duocarmycin natural products was synthesized via an enantioselective Friedel-Crafts alkylation. Easily accessible starting materials and good stereoselectivity in the alkylation step provide an enantioselective synthesis of the DNA-alkylating subunit.
Stereoselective access to γ-nitro carboxylates, precursors for highly functionalized γ-lactams
Meisterhans, Christian,Linden, Anthony,Hesse, Manfred
, p. 644 - 656 (2007/10/03)
A straightforward synthesis of the enantiomerically pure nitro derivatives 31 and epi-32, which are particularly useful intermediates for the synthesis of highly functionalized γ-lactams, is presented. (+)-(R)-3-Hydroxy-3-phenylpropanoic acid (20) and its ethyl ester 25 were prepared from (+)-L-mandelic acid (21). Condensation of 20 with pivalaldehyde furnished the novel enantiomerically pure 1,3-dioxan-4-one 17, the absolute configuration of which was established by X-ray crystal-structure analysis. Treating the lithium enolate of 17 with the nitro alkene 18 led, in a Michael-type addition, to a 1:1 mixture of two diastereoisomeric products. The stereocontrol of the addition was limited to the novel stereogenic center next to the lactone function. When the lithium enolate of 25 was treated with 18, the same selectivity was observed but with a lower chemical yield. Very facile separation of the isomers was achieved later in the synthetic sequence, when one isomer cyclized selectively to the nitro lactone 31, while the other one was isolated as hydroxy ester epi-32. The relative configuration of racemic epi-32 could be established by X-ray crystal-structure analysis.
Synthesis of 2-nitroalcohols by regioselective ring opening of epoxides with MgSO4/MeOH/NaNO2 system: A short synthesis of immunosuppressive agent FTY-720
Kalita,Barua,Bezbarua,Bez
, p. 1411 - 1414 (2007/10/03)
It has been demonstrated that a variety of epoxides can easily be opened with a system consisting of MgSO4/MeOH/NaNO2 giving the corresponding 2-nitroalcohols in excellent yields. This strategy has been applied to achieve a short synthesis of Immunosuppressive Agent FTY - 720.
Enantioselective synthesis of α-amino acids and monosubstituted 1,2- diamines by conjugate addition of 4-phenyl-2-oxazolidinone to nitroalkenes
Lucet, Denis,Sabelle, Stephane,Kostelitz, Olivier,Le Gall, Thierry,Mioskowski, Charles
, p. 2583 - 2591 (2007/10/03)
The addition of the potassium salt of (R)- or (S)-4-phenyl-2- oxazolidinone to monosubstituted nitroalkenes proceeded with very good diastereoselectivity. Several of the addition products were converted into α-amino acids and monosubstituted 1,2-diamines of high enantiomeric purity.
Approaches to carbocyclic analogues of the potent neuraminidase inhibitor 4-guanidino-Neu5Ac2en. X-Ray molecular structure of N-acetamide
Chandler, Malcolm,Conroy, Richard,Cooper, Anthony W. J.,Lamont, R. Brian,Scicinski, Jan J.,et al.
, p. 1189 - 1198 (2007/10/02)
Various approaches using Diels-Alder chemistry have been established for the synthesis of truncated carbocyclic analogues 4 and 6 of 4-guanidino-Neu5Ac2en.In the case of compound 4, elaboration of an initial adduct from Danishefsky's diene and the dienophile 7 allowed access to the key enone 26.Methylenation of the carbonyl group and azide-induced opening of an intermediate oxazoline established the required framework regio- and stereo-specifically.Compounds 4 and 6 were found to retain intetresting levels of antiviral activity comparable to those shown by their oxygen-containing counterparts.
