This paper reviews the past ten years of our research in the field of glycomimetics synthesis and design. The structure‐based design of mono‐ and polyvalent lectin ligands is one of the three main areas that we have explored in this period. We summarize here our work on ligands targeted against the dendritic cell receptor DC‐SIGN. A second direction we have followed involves the discovery of lectin

Theoretical and experimental work has been conducted about possible prebiotic syntheses of cysteine. Activated derivatives of this amino acid are able to oligomerize and polymerize to afford various poly‐thiazolines and cysteine‐rich chains.

Chiral aliphatic heterocycles are important structural feature of many pharmaceutical agents. Antibiotic resistance is a serious medical problem, therefore new antibacterial compounds are urgently needed. Herein, we describe synthesis of a series of 3,4‐disubstituted pyrrolidine derivatives via organocatalytic Michael addition followed by reductive cyclization. These compounds inhibited growth of standard

A convenient approach to 1,3‐bifunctional sulfonyl fluorides, sulfonamides and sulfinates bearing a bicyclo[1.1.1]penta­ne unit attached to the sulfur atom and (protected) amino or carboxyl group is described. The method relied on photochemical decomposition of Barton (1‐hydroxypyridine‐2(1 H )‐thione) esters of the corresponding carboxylic acids as the key step, followed by oxidation and cleavage

In this paper, we describe the synthesis of neglected 1‐aminoisochromene derivatives starting from 2‐alkynylbenzaldehydes and electron‐poor anilines. The domino reaction is catalyzed by original [Ag(I)PcL] complexes and occurs with complete regioselectivity under mild conditions. The approach well‐tolerates different aryl, heteroaryl, alkyl and cycloalkyl substituents on alkyne terminus to give the

An efficient and protecting‐group‐directed highly diastereoselective (≥99:1) synthesis of tetrahydro‐3 H ‐pyrrolo[ 2,3 ‐ c ]quinolines bearing four contiguous chiral centers was achieved by using intermolecular Michael addition followed by intramolecular Mannich cyclization strategy. The domino reaction proceeded well with a broad scope of substrates under mild conditions and afforded the corresponding

Hypervalent iodine‐guided electrophilic substitution (HIGES) was previously described for the para ‐selective benzylation of aryl‐ λ 3 ‐iodane diacetates. One drawback of the method was the synthesis and isolation of hypervalent iodine starting materials. An improvement is reported herein in which the benzylation product can be afforded from an aryl iodide via an in situ oxidation. Hypervalent iodine’s

The synthesis of 3,3’‐bioxindoles employing deacylative alkylations (DaA) in one‐pot process, where the 3‐bromooxindoles are generated in situ, is described. Good yields and moderate diastereoselections are obtained. By the modification of this procedure the synthesis of pure 3‐bromooxindoles through a deacylative bromination (DaB) is achieved. These bromides are efficiently employed in a photoredox

Abstract: Choline chloride (ChCl) based deep eutectic solvent (DES), facilitated the regioselective synthesis of ( E )‐1‐(4‐phenyl‐2‐styrylquinolin‐3‐yl)ethan‐1‐one ( 4 ), and ( E )‐3‐phenyl‐1‐(4‐phenyl‐2‐((E)‐styryl)quinolin‐3‐yl)prop‐2‐en‐1‐ones, ( 5 ) from the corresponding 2‐amino‐5‐chloro benzhydrol, ( 1 ) in one‐pot strategy. The 2‐methyl‐3‐acetylquinoline generated in situ from the 2‐amino‐5‐chloro

Herein oxidative ring‐opening of 1 H ‐pyrazol‐5‐amines to form 3‐diazenylacrylonitrile derivatives under mild and transition‐metal‐free conditions is described. In addition, the nucleophilic addition of deprotonated 1 H ‐pyrrole‐2‐carbaldehydes to the vinyl moiety of the yielded 3‐diazenylacrylonitriles could trigger domino cyclization to afford the 3 H ‐pyrazolo[3,4‐ e ]pyrrolo[1,2‐ a ]pyrazine derivatives

The 1,6‐electrocyclization of 1‐(2‐pyridyl)‐2‐azabuta‐1,3‐dienes obtained by Rh(II)‐catalyzed reaction of pyridotriazoles with 2 H ‐azirines affords stable non‐aromatic 4 H ‐pyrido[1,2‐ a ]pyrazines despite the fact that the reaction proceeds with irreversible dearomatization of the pyridine aromatic system. This pseudopericyclic cyclization occurs when the 2‐azabutadiene contains H, alkyl, or Ph at

A superbase mediated indirect Friedländer reaction towards functionalized quinolines has been realized. The reaction was performed with o‐aminobenzyl alcohol and ketones having an active methylene moiety in the presence of KOH and in DMSO. The reaction proceeds predominantly via initial formation of an imine intermediate and subsequent oxidation of the benzyl alcohol functionality and condensation

We have worked out a new approach to 1,3,4‐trisubstituted β‐carbolines of pharmaceutical interest. As central building blocks we used 2‐acylindoles, which are readily available from indole‐2‐Weinreb amides. Bromination at C‐3, followed by Suzuki‐Miyaura cross‐coupling with isoxazole‐4‐boronates gives 2‐acyl‐3‐isoxazolylindoles. Ring closure to the β‐carbolines was accomplished by reductive ring transformation

The synthesis of short‐chained anthracene‐strapped porphyrins and their Zn(II)complexes are reported. The key synthetic step employed was a [2+2] condensation between a dipyrromethane and the anthracene bisaldehyde, 2,2'‐((anthracene‐9,10‐diylbis(methylene))bis(oxy))dibenzaldehyde. Following exposure to white light, self‐sensitized singlet oxygen and the anthracene moieties underwent [4+2] cycloaddition

A new library of phosphonium salts has been synthesized from the reaction of tris‐(2,6‐dimethoxyphenyl)carbenium with different phosphines. The resultant phosphoninum salts work as efficient phase transfer catalysts for the alkylation of 1,3‐dicarbonyl compounds. One compound, a bifunctional phosphonium salt prepared from tris‐(2,6‐dimethoxyphenyl)carbenium and an aminophosphine, was also found to

Cross‐couplings between amides and 1,2‐dihaloalkenes are an efficient and straightforward way to access β‐haloenamides which, in turn, can be functionalized into complex, stereodefined enamide motifs. However, the intramolecular version of these cross‐couplings, leading to cyclic β‐haloenamides, has not been formally studied. In this paper, we report an investigation of factors affecting the efficiency

Direct C‐H β‐carbonyl alkylation of heteroarenes under metal‐, acid‐ and photo‐catalyst free conditions has been achieved. A wide scope of substrates, such as various substituted quinolines and isoquinolines, pyridines, pyridazine, benzo[d]thiazole and phenanthroline, underwent the β‐carbonyl alkylation efficiently via K 2 S 2 O 8 ‐mediated ring‐opening of cyclopropanols. The corresponding β‐heteroarylated

A stepwise non‐enzymatic conversion of the natural amino acid L ‐tyrosine into physiologically relevant intermediates L ‐DOPA, dopaquinone and dopachrome has been demonstrated in aqueous solution under ambient conditions. The photocatalytic redox process applied involves controlled activation of molecular oxygen forming water and hydrogen peroxide as further reaction products. Substrate conversion

A reagent‐directed divergent synthesis of three skeletally distinct compounds, namely, amino‐substituted indolizidine alkaloids, decahydropyrazino[2,1,6‐ cd ]‐pyrrolizine triols and (–)‐pochonicine stereoisomers have been accomplished from a single precursor. Tri‐ O ‐benzyl‐D‐glucal was converted into a diastereomeric mixture of homoallylic alcohols through a seven step sequence developed earlier in

Xylemin (6) and its designed structural analogues 18–23, N‐(4‐aminobutyl)alkylamines, were synthesized by 2‐nitrobenzenesulfonamide (Ns) strategy. Investigation of the improved synthesis of 20–23 resulted in the development of one‐step synthesis of these analogues from the commercially available corresponding ketones. Biological assessment of the synthetic molecules elucidated that xylemin (6) and

Electrochemical selenation in undivided electrochemical cells allows the preparation of selenium‐containing naphthoquinones. The rapid, green and efficient protocol avoids chemical oxidants and enables the synthesis of target molecules in a fast and reliable way. This strategy provides and efficient and general method for the synthesis of quinoidal compounds with activity against five cancer cell lines

A highly efficient copper‐catalyzed one‐pot sequential approach has been developed for the synthesis of azole‐fused imidazo[1,2‐ a ]pyridines with 2‐(2‐bromophenyl)imidazo[1,2‐ a ]pyridine‐3‐carbaldehydes as substrates. The one‐pot approach involved a sequential three‐component imidazole/benzimidazole formation followed by a copper‐catalyzed intramolecular Ullmann type C–N coupling. The method tolerated

Isomerization to linear ketones is a valuable transformation of 1,2‐disubstituted cyclopropanols proceeding through radical intermediates. Despite simplicity of this reaction, the known protocol required stoichiometric amounts of both an oxidant and a reducing agent. In this article, we report a catalytic isomerization of 1,2‐cyclopropanols to linear ketones enabled by the photoredox catalytic system

The first regio‐ and enantioselective organocatalytic cascade α,γ ‐dialkylation of α , β ‐unsaturated aldehydes is achieved. Substrates scope is demonstrated with a variety of α , β ‐unsaturated aldehydes and alkylating agents. The absolute configuration of the α,γ ‐dialkylated product is confirmed using single‐crystal X‐ray analysis of its carbamate derivative. The practicality of this methodology

Involving the cyano group of N‐cyano sulfoximines in [3+2]‐cycloaddition reactions with 1,3‐dipoles provides practical routes for the construction of 5‐membered heterocycles bearing sulfoximinoyl moieties. An ytterbium‐catalyzed cycloaddition utilizing hydrazonoyl chlorides was developed, as well as a reaction involving imidoyl chlorides proceeding without the aid of a catalyst. Following these protocols

The drimentine family is a class of hybrid isoprenoids derived from actinomycete bacteria. Members of this family display weak antitumor and antibacterial activity Herein we report our efforts toward the total synthesis of drimentine C using three distinct approaches incorporating palladium‐catalyzed cyanoamidation, reductive cross‐coupling, and photoredox‐catalyzed α‐alkylation of an aldehyde as key

A number of structurally diverse D‐mannose‐derived lactols, including various deoxy‐D‐mannoses and conformationally restricted bicyclic D‐mannoses, have been synthesized and investigated in mechanistic studies of β ‐mannosylation via Cs 2 CO 3 ‐mediated anomeric O ‐alkylation. It was found that deoxy mannoses or conformationally restricted bicyclic D‐mannoses are not as reactive as their corresponding

The reactivity of donor‐acceptor (D‐A) cyclopropanes towards acceptor‐substituted ketenedithioacetals was investigated. In a Lewis‐acid‐catalyzed (3+2)‐cycloaddition, the corresponding dithiaspiro compounds were synthesized in good yields. The 1,3‐dithiane unit, a masked keto functionality, was cleaved by N ‐iodosuccinimide. Thus, this two‐step process represents a formal insertion of an acceptor‐substituted