The cyclization of a ribose-derived pentenose oxime with various halogen electrophiles showed bromine to be the most effective reagent, leading to 80% of L-lyxo/D-ribo-pyrroline N-oxides in an 84:16 diastereomeric ratio. In order to explore the scope of this facile process, several other γ ,δ unsaturated oximes were submitted to this reaction. Depending on the substitution pattern, 23 – 87%, yi...

Isoxazole-5(4H)-ones are heteropentacycle compounds found in several bioactive molecules with pharmaceutical and agrochemical properties. A well-known multicomponent reaction between β-ketoester, hydroxylamine, aromatic aldehydes leads to 3-methyl-4-arylmethylene isoxazole-5(4H)-ones, mild conditions. The initial purpose of this work was investigate whether the might be induced by light, as des...

Highly efficient asymmetric aldol reactions between α,β-unsaturated keto esters and acyclic ketones catalyzed by chiral diamines are reported. The corresponding products were obtained in excellent yields with excellent enantioselectivities. The absolute configuration for the product was determined by X-ray analysis. A variety of substrates were tolerable in the present catalytic system.

BACKGROUND The carbonyl group at position 2 of N-acetylisatin behaves as an amide which is more susceptible to nucleophilic attack via ring-opening in the presence of nucleophiles. Because of this behavior, in the present work we describe the microwave synthesis of a series of α-ketoamide and bis-(α-ketoamide) derivatives via the facile ring-opening of N-acylisatin with different amines and dia...

Background: The carbonyl group at position 2 of N-acetylisatin behaves as an amide which is more susceptible to nucleophilic attack via ring-opening in the presence of nucleophiles. Because of this behavior, in the present work we describe the microwave synthesis of a series of α-ketoamide and bis-(α-ketoamide) derivatives via the facile ring-opening of N-acylisatin with different amines and di...

The all-alkyl α-tertiary amino acid scaffold represents an important structural feature in many biologically and pharmaceutically relevant molecules. Syntheses of this class molecule, however, often involve multiple steps require activating auxiliary groups on the nitrogen atom or tailored building blocks. Here, we report a straightforward, single-step, modular methodology for synthesis esters....

Abstract Fluoroquinolones such as levofloxacin and ciprofloxacin are potent antibiotics prescribed to treat various bacterial infections. Recent studies have also identified prominent examples promising anti‐cancer agents. However, significant off‐target effects observed in human patients precluded their wide‐spread clinical use. For instance, upon systemic administration, overt toxicity toward...

Three photoaffinity labeled derivatives of epothilone D were prepared by total synthesis, using efficient novel asymmetric synthesis methods for the preparation of two important synthetic building blocks. The key step for the asymmetric synthesis of (S,E)-3-(tert-butyldimethylsilyloxy)-4-methyl-5-(2-methylthiazol-4-yl)pent-4-enal involved a ketone reduction with (R)-Me-CBS-oxazaborolidine. For ...

The dialkyl 2,6-dialkylsubstituted 4-piperidone-3,5-dicarboxylates were synthesized by a Mannich procedure. Depending on the substitution at the nitrogen keto-enol-tautomerism and a configurational isomerism at C 2 is observed. The structure o f the N-substituted piperidone 24 E (C 18H29N 0 5) has been determined by X-ray analysis: it is characterized by an enol structure o f the /?-ketoester a...