- Total Synthesis of Indolizidine Alkaloids via Nickel-Catalyzed (4 + 2) Cyclization
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A Ni-catalyzed (4 + 2) cycloaddition of alkynes and azetidinones toward piperidinones was used as key reaction in the enantioselective synthesis of naturally occurring indolizidine alkaloids. The reaction benefits from the use of an easily accessible azet
- Renner, Jonas,Thakur, Ashish,Rutz, Philipp M.,Cowley, Jacob M.,Evangelista, Judah L.,Kumar, Puneet,Prater, Matthew B.,Stolley, Ryan M.,Louie, Janis
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supporting information
p. 924 - 928
(2020/02/04)
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- Syntheses of Enantiopure 1,2-Ethylenediamines with Tethered Secondary Amines of the Formula H 2NCH 2CH[(CH 2) nNHMe]NH 2(n = 1-4) from α-Amino Acids: New Agents for Asymmetric Catalysis
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Tris(hydrochloride) adducts of the title compounds-are prepared from the inexpensive α-amino acids H 2 N(C=O)CH 2 CH(NH 2)CO 2 H, HO(C=O)(CH 2) n ′ CH(NH 2)CO 2 H (n ′ = 1, 2), and H2 N(CH 2) 4 CH(NH 2)CO 2 H, respectively (steps/overall yield = 5/32, 7/30, 7/33, 5/38). The NH 2 group that is remote from the secondary amine is installed via BH 3 reduction of an amide [-(C=O)NR 2[ derived?-from an α-amino carboxylic acid. The MeNHCH 2 units are introduced by BH 3 reductions of alkyl carbamate [RO(C=O)NHCH 2-; R = Et, t-Bu] or amide [MeHN(C=O)-] moieties.
- Kabes, Connor Q.,Gunn, Jack H.,Selbst, Maximilian A.,Lucas, Reagan F.,Gladysz, John A.
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p. 3277 - 3285
(2020/11/02)
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- METHOD FOR PREPARING 3-[(3S)-7-BROMO-2-OXO-5-(PYRIDIN-2-YL)-2,3-DIHYDRO-1H-[1,4]-BENZODIAZEPIN-3-YL] PROPIONIC ACID METHYL ESTER, AND COMPOUNDS USEFUL IN THAT METHOD
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The present invention relates to a method for preparing 3-[(3S)-7- bromo-2-oxo-5-(pyridin-2-yl)-2,3-dihydro-IH-[l,4]-benzodiazepin-3-yl] propionic acid methyl ester from (2-amino-5-bromo-phenyl)-pyridin-2- yl-methanone. The present invention also relates
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Page/Page column 16; 17
(2019/02/13)
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- METHOD FOR PREPARING 3-[(4S)-8-BROMO-1-METHYL-6-(PYRIDIN-2-YL)-4H-IMIDAZO[1,2-A][1,4]BENZODIAZEPIN-4-YL]-PROPIONIC ACID METHYL ESTER, AND COMPOUNDS USEFUL IN SAID METHOD
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The present invention relates to a method for preparing 3- [ ( 4S ) -8-bromo-l-methyl-6- (pyridin-2-yl ) -4H-imidazo [1,2- a] [ 1, 4 ] benzodiazepin-4-yl ] -propionic acid methyl ester starting from 3- [ (3S) -7-bromo-2-oxo-5- (pyridin-2-yl ) -2, 3-dihydr
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Page/Page column 34; 35
(2019/05/02)
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- Constrained Cyclic β,γ-Diamino Acids from Glutamic Acid: Synthesis of Both Diastereomers and Unexpected Kinetic Resolution
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We describe here an efficient synthesis of both diastereomers of cyclic β,γ-diamino acids starting from l-glutamic acid, based on the Blaise reaction. We show that by changing the protecting group, we can access either the five-membered-ring lactam, which
- Wan, Yang,Auberger, Nicolas,Thétiot-Laurent, Sophie,Bouillère, Francelin,Zulauf, Ana?s,He, Jiefang,Courtiol-Legourd, Stéphanie,Guillot, Régis,Kouklovsky, Cyrille,Cote des Combes, Sylvain,Pacaud, Christophe,Devillers, Ingrid,Alezra, Valérie
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p. 329 - 340
(2018/01/27)
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- SERINE REPLACEMENT POLYMYXIN ANALOGUES USEFUL AS ANTIBIOTIC POTENTIATORS
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The disclosure provides compounds of the formula I or a tautomer thereof, or a pharmaceutically acceptable salt of either of the foregoing. The variables R1 and R2 are defined in the disclosure. The disclosure further includes pharmaceutical compositions comprising a compound of formula I together with at least one pharmaceutically acceptable carrier. The disclosure also includes a method of sensitizing bacteria to an antibacterial agent, comprising administering a therapeutically effective amount of the antibacterial agent and a compound of formula I to a patient infected with the bacteria, simultaneously or sequentially.
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Paragraph 0121
(2017/12/09)
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- Photoinduced release of neurotransmitter amino acids from coumarin-fused julolidine ester cages
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The photoinduced release of several neurotransmitter amino acids (glycine, alanine, glutamic acid, β-alanine and γ-aminobutyric acid) was accomplished from ester cages based on a new photoremovable protecting group consisting of a coumarin built on the julolidine nucleus, namely a (11-oxo-2,3,5,6,7,11-hexahydro-1H-pyrano[2,3-f]pyrido[3,2,1-ij]quinolin-9-yl) methyl group. Photolysis and steady-state sensitization studies revealed that release of the active molecule occurred in short irradiation times at long wavelengths, with a very promising performance at 419 nm. Given the interest in the development of novel protecting groups that are cleavable with UV A or even visible radiation, it was found that a structural modification in the coumarin ring by assembly of a fused julolidine leads to a promising photolabile protecting group for organic synthesis and also for bioapplications. Photolysis and steady-state sensitization studies of several neurotransmitter amino acids from ester cages based on a new photoremovable protecting group consisting of a coumarin-fused julolidine nucleus, revealed that the release of the active molecule occurred in short irradiation times at long wavelengths, especially at 419 nm. Copyright
- Piloto, Ana M.,Hungerford, Graham,Costa, Susana P. G.,Goncalves, M. Sameiro T.
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p. 7715 - 7723
(2013/12/04)
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- ACE-INHIBITORS HAVING ANTIOXIDANT AND NO-DONOR ACTIVITY
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Multifonctional ACE inhibitor compounds are provided, that combine ACE-inhibiting activity with capability to scavenge superoxide and other reactive oxygen species, and that may further function as nitric oxide donors. The compounds are useful for preventing or treating various disorders, including cardiovascular, and diabetes associated disorders.
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Page/Page column 57; 58
(2010/02/07)
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- Utility of tetrathiomolybdate and tetraselenotungstate: Efficient synthesis of cystine, selenocystine, and their higher homologues
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Efficient synthesis of cystine, selenocystine, and their higher homologues like homo and bishomo amino acid derivatives from natural amino acid derivatives using tetrathiomolybdate and tetraselenotungstate reagents under mild and neutral conditions is reported. The generality of the reaction has been studied by capping various groups to amino and carboxyl components of canonical amino acids.
- Bhat, Ramakrishna G.,Porhiel, Emmanuel,Saravanan, Vadivelu,Chandrasekaran, Srinivasan
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p. 5251 - 5253
(2007/10/03)
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- A synthetic approach to diaryl ethers using the Robinson annulation
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An alternative synthetic approach to diaryl ethers has been developed. In the key transformation, Robinson annulation of nonracemic aldehydes 16a,b, derived from L-glutamic acid 5-methyl ester and phenoxymethylvinyl ketone, provided α-phenoxyenones 17a,b.
- Feng, Xianqi,Edstrom, Eric D.
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- The asymmetric synthesis of γ-substituted glutamic acid derivatives via a glutamic acid γ-enolate synthon
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Treatment of α-t-butyl γ-methyl N-Z glutamate with lithium hexamethyldisilazide gives the γ-enolate regioselectively. Reaction of this enolate with electrophiles gives γ-substituted glutamic acid derivatives including the conformationally constrained glut
- Del Bosco, Marco,Johnstone, Andrew N.C.,Bazza, Giorgia,Lopatriello, Stefania,North, Michael
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p. 8545 - 8554
(2007/10/02)
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- SYNTHESE DE L'ACIDE 3-(3,6-DIOXOPIPERAZIN-2-YL) PROPANOIQUE
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The 3-(3,6-dioxopiperazin-2-yl) propanoic acid (8) was synthesized from L-5-methyl glutamate (1) and ethyl glycinate.The regioselectivity was controled by using t-BOC-ON and EEDQ.
- Jerumanis, Stanislas,Lefebvre, Jean
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p. 127 - 130
(2007/10/02)
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- 1-Hydroxy-3-amino-2-piperidone (δ-N-Hydroxycycloornithine) Derivatives: Key Intermediates for the Synthesis of Hydroxamate-Based Siderophores
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Several routes for the synthesis of δ-N-(benzyloxy)cycloornithine (2) from glutamic acid derived starting materials are described.Efficient methods were developed for the synthesis of glutamic acid γ-semialdehyde and γ-hydroxynorvaline derivatives as key substrates for the preparation of δ-N-hydroxyornithine analogues.Thus, the best approaches to the synthesis of 2 were: (1) reductive cyclization of an N-hydroxysuccinimide ester of the O-benzyloxime 4 of α-amino-protected glutamic acid γ-semialdehyde 5 and (2) cyclization of the N-(benzyloxy)amide of δ-bromonorvaline (7).
- Kolasa, Teodozyj,Miller, Marvin J.
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p. 1711 - 1721
(2007/10/02)
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- Novel and Selective Enzymatic Hydrolysis of γ-Esters of Dimethyl α-Dehydroglutamate with α-Chymotrypsin A
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Selective enzymatic hydrolysis of γ-ester of Cbz-ΔGlu(OMe)-OMe with α-chymotrypsin at pH 9 was readily achieved to give the corresponding α-half ester (Cbz-ΔGlu-OMe) along with a small amount of Cbz-ΔGlu(OMe)-OH and Cbz-ΔGlu-OH.
- Shin, Chung-gi,Seki, Masashi,Takahashi, Nobuyuki
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p. 2089 - 2090
(2007/10/02)
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- MONO-ESTERIFICATION OF N-PROTECTED DI-ACIDS ASPARTIC AND GLUTAMIC BY CHLOROFORMATE ACTIVATION
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Mono-esters of N-protected di-acids aspartic and glutamic are prepared by a one-pot activation with alkyl chloroformates or isopropenyl chloroformate and an additionnal alcohol.This process involves the intermediate internal anhydride formation.
- Jouin, P.,Castro, B.,Zeggaf, C.,Pantaloni, A.,Senet, J.P,et al
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p. 1665 - 1668
(2007/10/02)
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- Useful Intermediates for Synthesis of Dicarba Analogues of Cystine Peptides: Selectively Protected α-Aminosuberic Acid and α,α'-Diaminosuberic Acid of Defined Stereochemistry
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Practical procedures are described for synthesis of selectively protected α-aminosuberic acid and α,α'-diaminosuberic acid by the mixed Kolbe electrolytic decarboxylative dimerization of two different carboxylic acids.Stereochemistry is established by the choice of L- or D-glutamic acid precursors.The method is illustrated by the synthesis of α-tert-butyl Nα-Boc-Nα'-Cbz-LL-α,α'-diaminosuberate (6) and α-tert-butyl ω-methyl Nα-Boc-D-α-aminosuberate (10) which can be used directly in the preparation of dicarba and desaminodicarba analogues of cystinepeptides.Although statistically controlled mixtures are produced, facile procedures for isolation of the products have been worked out.No racemization of chiral centers was detected.
- Nutt, Ruth F.,Strachan, Robert G.,Veber, Daniel F.,Holly, Frederick W.
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p. 3078 - 3080
(2007/10/02)
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