154802-92-3Relevant academic research and scientific papers
Concise syntheses of enantiomerically pure protected 4-hydroxypyroglutamic acid and 4-hydroxyproline from a nitroso-cyclopentadiene cycloadduct
Huang, Weiqiang,Miller, Marvin J.
, p. 2835 - 2838 (2008)
O-TBS-protected methyl trans-4-hydroxypyroglutamate and methyl trans-4-hydroxyproline ester were synthesized from nitroso-cyclopentadiene Diels-Alder cycloadducts. Enzymatic resolution of the key intermediate, 4-amino-cyclopent-2-enol, provides access to both l- and d-amino acids.
Efficient functionalization of acylnitroso cycloadducts: Application to the syntheses of carbocyclic nucleoside precursors
Zhang, Deyi,Ghosh, Arun,Sueling, Carsten,Miller, Marvin J.
, p. 3799 - 3802 (1996)
1,4-cis-disubstituted cyclopentene precursors of carbocyclic nucleosides were readily prepared utilizing acylnitroso hetero Diels-Alder reactions and Pd(0)-catalyzed alkylation reactions as the key steps. The chemistry was explored in both racemic and asymmetric fashion. The hydroxymethyl components of the carbocyclic nucleoside precursors were obtained from nitromethyl groups under oxidative Nef conditions and may be further elaborated into a variety of compounds of potential biological interest.
Asymmetric synthesis of an important precursor to 5'-nor carbocyclic nucleosides
Vogt, Paul F.,Hansel, Jan-Gerd,Miller, Marvin J.
, p. 2803 - 2804 (1997)
An asymmetric hetero-Diels-Alder reaction involving an amino acid-derived acylnitroso dienophile was utilized to synthesize (1S, 4R)-4-[N-(tert-butoxycarbonyl)amino]-2-cyclopentene-1-ol (4). The amino acid chiral auxiliary was removed by the Edman degradation. This enantiomerically pure aminoalcohol is a key intermediate in the synthesis of 5'-nor carbocyclic nucleosides.
Lewis acid-promoted hetero Diels-Alder cycloaddition of α-acetoxynitroso dienophiles
Calvet, Geraldine,Dussaussois, Marion,Blanchard, Nicolas,Kouklovsky, Cyrille
, p. 2449 - 2451 (2004)
(Equation Presented) α-Acetoxynitroso compound 3 has been prepared as a new stable, isolable, and reactive dienophile in nitroso Diels-Alder reactions. The yield of the [4 + 2] cycloaddition of α-acetoxynitroso dienophile with 1,3-dienes could be enhanced in the presence of 20 mol % Lewis acid. An unexpected retro hetero-Michael reaction from 26 was observed, leading to the cleavage of the N-O bond of the cycloadduct. This tandem nitroso Diels-Alder/retro hetero-Michael sequence has been used with cyclic and acyclic 1,3-dienes.
Synthetic application of acylnitroso Diels-Alder derived aminocyclopentenols: Total synthesis of (+)-streptazolin
Li, Fangzheng,Warshakoon, Namal C.,Miller, Marvin J.
, p. 8836 - 8841 (2004)
Concise total syntheses of (+)-streptazolin 1 and its more stable dihydro derivative 2 were accomplished via an intramolecular aldol condensation strategy starting from readily available aminocyclopentenol (-)-7. The synthetic sequence included reductive amination, stereoselective epoxidation, intramolecular aldol (and condensation) reaction, and Wittig reaction. The overall yield for dihydro derivative 2 from aminocyclopentenol (-)-7 was about 7% for a total of 14 steps.
Reactions of nitroso hetero-Diels-Alder cycloadducts with azides: Stereoselective formation of triazolines and aziridines
Bodnar, Brian S.,Miller, Marvin J.
, p. 3929 - 3932 (2007)
(Chemical Equation Presented) The addition of azides to acylnitroso hetero-Diels-Alder cycloadducts derived from cyclopentadiene affords exo-triazolines in excellent yield. The reaction is greatly affected by the level of alkene strain, while sterically d
Palladium-catalyzed decarboxylative rearrangements of allyl 2,2,2-trifluoroethyl malonates: direct access to homoallylic esters
Tardibono Jr., Lawrence P.,Patzner, Jerod,Cesarlo, Cara,Miller, Marvin J.
, p. 4076 - 4079 (2009)
Homoallylic esters are obtained In a single transformation from allyl 2,2,2-trifluoroethyl malonates by using a Pd(O) catalyst. Facile decarboxylation of allyl 2,2,2-trifluoroethyl malonates is attributed to a decrease in pK a compared to allyl
Method for preparing (1R, 3S)-3-aminocyclopentanol hydrochloride
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, (2021/03/31)
The invention discloses a method for preparing (1R, 3S) 3-aminocyclopentanol hydrochloride, belongs to the field of organic chemical synthesis, and provides a process route to overcome the defects ofhigh price, difficulty in chiral control and the like in the prior art. The process route comprises the following steps: 1) oxidizing tert-butyl carbonate hydroxylamine into tert-butyl carbonate nitrosyl under the catalysis of copper chloride and 2-ethyl-2-oxazoline, then carrying out a hetero Diels-Alder reaction with cyclopentadiene in situ; 2) selectively reducing nitrogen-oxygen bonds in a zinc powder-acetic acid reaction system; 3) under the catalysis of lipase, reacting with vinyl acetate to optically and selectively realize chiral resolution; 4) reducing double bonds through palladium carbon hydrogenation; 5) under the alkaline condition of lithium hydroxide-methanol, performing deacetylation protection; and 6) removing tert-butyl carbonate protection in a hydrogen chloride isopropanol acid solution prepared from acetyl chloride and isopropanol in situ, and forming hydrochloride in situ to obtain a target product. The synthetic method has the beneficial effects that the synthetic method has the characteristics of novel and short route, high optical purity, low cost and the like.
Addition of Lithium Anion of (Acetylmethylene)triphenylphosphorane to Nonracemic Sulfinimines: Total Synthesis of (+)-241D and Formal Total Synthesis of (+)-Preussin
Khandare, Sopan P.,Prasad, Kavirayani R.,Reddy, Polimera Obula
supporting information, p. 7273 - 7277 (2020/10/02)
The addition of lithium anion of (acetylmethylene)triphenylphosphorane to nonracemic sulfinimines was investigated. It was found that the addition proceeded with good diastereoselectivity and further reaction of the formed sulfinimidophosphorane with seve
Novel Imidazo[4,5-c]Quinoline And Imidazo[4,5-c][1,5]Naphthyridine Derivatives As LRRK2 Inhibitors
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Paragraph 0175, (2017/04/04)
The present invention provides novel imidazo[4,5-c]quinoline and imidazo[4,5-c][1,5]naphthyridine derivatives of Formula (I), and the pharmaceutically acceptable salts thereof wherein R1, R1a, R1b, R2, R4, R5, R6, X and Z are as defined in the specification. The invention is also directed to pharmaceutical compositions comprising the compounds of Formula (I) and to use of the compounds in the treatment of diseases associated with LRRK2, such as neurodegenerative diseases including Parkinson's disease or Alzheimer's disease, cancer, Crohn's disease or leprosy.
