40856-59-5Relevant articles and documents
Reaction of (S)-homoserine lactone with Grignard reagents: synthesis of amino-keto-alcohols and β-amino acid derivatives
Gündo?du, ?zlem,Turhan, P?nar,K?se, Aytekin,Altunda?, Ramazan,Kara, Yunus
, p. 1163 - 1168 (2017/09/15)
The ring-opening reaction of homoserine lactone with phenylmagnesium bromides was systematically examined. A reliable method to achieve β-amino acid precursors was developed by tuning the reaction conditions to favor mono-addition to the carbonyl moiety of the lactone.
Mitsunobu Reactions Catalytic in Phosphine and a Fully Catalytic System
Buonomo, Joseph A.,Aldrich, Courtney C.
supporting information, p. 13041 - 13044 (2015/11/02)
The Mitsunobu reaction is renowned for its mild reaction conditions and broad substrate tolerance, but has limited utility in process chemistry and industrial applications due to poor atom economy and the generation of stoichiometric phosphine oxide and hydrazine by-products that complicate purification. A catalytic Mitsunobu reaction using innocuous reagents to recycle these by-products would overcome both of these shortcomings. Herein we report a protocol that is catalytic in phosphine (1-phenylphospholane) employing phenylsilane to recycle the catalyst. Integration of this phosphine catalytic cycle with Taniguchi's azocarboxylate catalytic system provided the first fully catalytic Mitsunobu reaction. Make it catalytic: A catalytic Mitsunobu reaction using innocuous reagents to recycle the stoichiometric phosphine oxide and hydrazine by-products was developed. The reported method is catalytic in 1-phenylphospholane and uses phenylsilane to recycle the catalyst. Integration of this phosphine catalytic cycle with Taniguchi's azocarboxylate catalytic system provided the first fully catalytic Mitsunobu reaction.
Efficient and Selective Cu/Nitroxyl-Catalyzed Methods for Aerobic Oxidative Lactonization of Diols
Xie, Xiaomin,Stahl, Shannon S.
supporting information, p. 3767 - 3770 (2015/04/14)
Cu/nitroxyl catalysts have been identified that promote highly efficient and selective aerobic oxidative lactonization of diols under mild reaction conditions using ambient air as the oxidant. The chemo- and regioselectivity of the reaction may be tuned by changing the identity of the nitroxyl cocatalyst. A Cu/ABNO catalyst system (ABNO = 9-azabicyclo[3.3.1]nonan-N-oxyl) shows excellent reactivity with symmetrical diols and hindered unsymmetrical diols, whereas a Cu/TEMPO catalyst system (TEMPO = 2,2,6,6-tetramethyl-1-piperidinyl-N-oxyl) displays excellent chemo- and regioselectivity for the oxidation of less hindered unsymmetrical diols. These catalyst systems are compatible with all classes of alcohols (benzylic, allylic, aliphatic), mediate efficient lactonization of 1,4-, 1,5-, and some 1,6-diols, and tolerate diverse functional groups, including alkenes, heterocycles, and other heteroatom-containing groups.
CRYSTALLINE FORMS OF A PYRROLIDONE DERIVATIVE USEFUL IN THE TREATMENT OF ALZHEIMER'S DISEASE AND PREPARATION THEREOF
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, (2015/05/19)
The present invention provides processes to manufacture crystalline N-[(3S)-1-[4-[(3-fluorophenyl)methoxy]phenyl]-5-oxo-pyrrolidin-3-yl]acetamide. Also disclosed are polymorphic forms of said compound as well as compounds useful as intermediates in the methods of the invention.
Solution structural features of N-acyl homoserine lactones
Tumminakatti, Shama,Khatri, Bhavesh,Krishnamurti, Vinayak,Athavale, Vishikh,Prabhakaran, Erode N.
supporting information, p. 5771 - 5775 (2015/09/29)
Here we demonstrate that in interbacterial quorum signal moderators, N-acylhomoserine lactones (AHLs), the stabilization of bioactive pharmacophore lactone against lysis is through the e- withdrawing N-acyl motif which reduces lactone carbonyl polarization. This lysis is assisted by weak (-1) contacts between N-acyl O and lactone C′. The interactions that preclude this weak contact, in the free and receptor-bound AHLs, improve lactone halflife and hence are key to the design of the antibacterial AHL analogues.
Using the 9-BBN group as a transient protective group for the functionalization of reactive chains of α-amino acids
Sanchez, Adrian,Calderon, Ernesto,Vazquez, Alfredo
, p. 1364 - 1372 (2013/07/05)
Achieving chemoselectivity is a longstanding challenge in chemical synthesis. This problem has been addressed using different approaches, but a definitive solution is still pending. For instance, in peptide chemistry, particularly with amino acids containing side chains functionalities with reactivity patterns similar to the main functional groups, such as aspartic and glutamic acids, and lysine and ornithine, specific semi-permanent protecting groups have been employed. The use of 9-borabicyclo[3.3.1]nonane (9-BBN-H) as a transient protective group for the selective protection of α-amino acids, which allows the chemoselective manipulation of the functional groups embedded in the side chains of the molecule, is described.
The natural product hybrid of Syringolin A and Glidobactin A synergizes proteasome inhibition potency with subsite selectivity
Clerc, Jerome,Li, Nan,Krahn, Daniel,Groll, Michael,Bachmann, Andre S.,Florea, Bogdan I.,Overkleeft, Herman S.,Kaiser, Markus
supporting information; experimental part, p. 385 - 387 (2011/03/17)
The preparation of a Syringolin A/Glidobactin A hybrid (SylA-GlbA) consisting of a SylA macrocycle connected to the GlbA side chain and its potent proteasome targeting of all three proteasomal subsites is reported. The influence of the syrbactin macrocycle moiety on subsite selectivity is demonstrated.
Raney-co mediated reductive cyclization of an α,β-unsaturated nitrile
Janey, Jacob M.,Orella, Charles J.,Njolito, Eugenia,Baxter, Jenny M.,Rosen, Jonathan D.,Palucki, Michael,Sidler, Rick R.,Li, Wenjie,Kowal, Jason J.,Davies, Ian W.
, p. 3212 - 3217 (2008/09/19)
(Chemical Equation Presented) An expedient, five step synthesis of caprolactam 1 is reported starting from natural L-homoserine. The key step is a chemoselective reductive cyclization of α,β-unsaturated nitrile 10 mediated by Raney-Co type metals. This hydrogenation is extensively investigated in order to account for the observed product distribution and yields.
A practical method for selective cleavage of a tert-butoxycarbamoyl N-protective group from N,N-diprotected α-amino acid derivatives using montmorillonite K-10
Hernandez, J. Nicolas,Crisostomo, Fernando R. Pinacho,Martin, Tomas,Martin, Victor S.
, p. 5050 - 5058 (2008/03/18)
A new, practical, and mild procedure for the selective cleavage of a tert-butoxycarbonyl group (Boc) in N-Boc-N-acyl-diprotected amines is described. When applied to α-amino acids, complete integrity of the stereochemistry was observed. The use of N,N-di-Boc-α-amino-δ- and γ-hydroxy esters provided both δ- and γ-lactones in very good yields. The method is based on the use of Montmorillonite K-10 either in CH 2Cl2 at room temperature or in toluene at 65°C and is compatible with the presence of a large range of functional and other protecting groups in the substrates. In most cases virtually pure samples are obtained after filtration and removal of solvents. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.
Synthesis and evaluation of acyl protein thioesterase 1 (APT1) inhibitors
Biel, Markus,Deck, Patrick,Giannis, Athanassios,Waldmann, Herbert
, p. 4121 - 4143 (2007/10/03)
Lipid-modified proteins play decisive roles in important biological processes such as signal transduction, organisation of the cytoskeleton and vesicular transport. Lipidation of these proteins is essential for correct biological function. Among the modifications with lipids, prenylation and myristoylation are well understood. However, the machinery of palmitoylation is still under investigation. Recently, an enzyme, acyl protein thioesterase 1 (APT1), that may play a regulatory role in the palmitoylation cycle of HRas and G-protein a subunits, was purified. Motivated by this work, several inhibitors of APT1 were designed, synthesized and biologically evaluated leading to highly active compounds.
