Organic & Medicinal Chemistry Group

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Research

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Research

Two projects are currently going on in the group: one is about the design and synthesis of cysteine proteases inhibitors and the other one is based on the asymmetric synthesis and derivatization of oxiranic compounds: 

 

We have synthesized three families of potent parasitic cysteine proteases inhibitors. Dipeptidyl Epoxyesters, Enones and Nitroalkenes:

We have reported an enantioselective synthesis of chiral vicinal diamines starting from nitroepoxides using a chiral amine and a reductive agent. The process is a dynamic kinetic asymmetric transformation (DYKAT):

We have also reported that sulfur-oxygen interactions are the main driving force during isomerization of cyclic alpha-sulfurated aldols:

 

We reported an efficient ring opening of 3,4-epoxyesters with alcohols to produce 4-alkoxy-3-hydroxyesters and their isomerization into 4-ketoesters using boron trifluoride as catalyst. Both transformations are simple and efficient methods for the synthesis of above named synthetically useful compounds.

If 3,4-epoxyketones are treated with boron trifluoride then furans are prepared.

The obtained epoxides have applied to the syntheses of interesting compounds, such as an alpha-methylene-beta-hydroxy-gamma-butyrolactone which is a natural product:

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We reported nitroepoxides are easily transformed into 1,4-diamino heterocycles such as quinoxalines and pyrazines by treatment with 1,2-benzenediamines and ammonia respectively. Additionally, related saturated heterocycles, such as piperazines and tetrahydroquinoxalines can be accessed by treatment with 1,2-diamines and a reducing agent. Recently we have reported the transformation of nitroepoxides into morpholines and benzoxazines:

We have also synthesized epoxysulfones as electrophilic traps for human cathepsins inhibitors:

Design and synthesis of cysteine proteases inhibitors

Asymmetric synthesis and derivatization of oxiranic compounds

A similar study was performed over Morita-Baylis Hillman adducts:

We have performed highly diastereoselective epoxidation reactions of electron-deficient alkenes having an  oxygenated stereocenter: