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9 pages, 1163 KiB

Open AccessArticle

Synthesis and Modeling of Ezetimibe Analogues

by Mateo M. Salgado, Alejandro Manchado, Carlos T. Nieto, David Díez and Narciso M. Garrido

Molecules 2021, 26(11), 3107; https://doi.org/10.3390/molecules26113107 - 22 May 2021

Cited by 7 | Viewed by 2755

Abstract

Ezetimibe is a well-known drug that lowers blood cholesterol levels by reducing its absorption in the small intestine when joining to Niemann-Pick C1-like protein (NPC1L1). A ligand-based study on ezetimibe analogues is reported, together with one-hit synthesis, highlighted in the study. A convenient [...] Read more.

Ezetimibe is a well-known drug that lowers blood cholesterol levels by reducing its absorption in the small intestine when joining to Niemann-Pick C1-like protein (NPC1L1). A ligand-based study on ezetimibe analogues is reported, together with one-hit synthesis, highlighted in the study. A convenient asymmetric synthesis of (2S,3S)-N-α-(R)-methylbenzyl-3-methoxycarbonylethyl-4-methoxyphenyl β-lactam is described starting from Baylis–Hillman adducts. The route involves a domino process: allylic acetate rearrangement, stereoselective Ireland–Claisen rearrangement and asymmetric Michael addition, which provides a δ-amino acid derivative with full stereochemical control. A subsequent inversion of ester and acid functionality paves the way to the lactam core after monodebenzylation and lactam formation. It also shows interesting results when it comes to a pharmacophore study based on ezetimibe as the main ligand in lowering blood cholesterol levels, revealing which substituents on the azetidine-2-one ring are more similar to the ezetimibe skeleton and will more likely bind to NPC1L1 than ezetimibe. Full article

(This article belongs to the Special Issue New Synthetic Methods for Organic Compounds)

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12 pages, 2150 KiB

Open AccessFeature PaperArticle

Intramolecular Nicholas Reaction Enables the Stereoselective Synthesis of Strained Cyclooctynes

by Diego M. Monzón, Juan Manuel Betancort, Tomás Martín, Miguel Ángel Ramírez, Víctor S. Martín and David Díaz Díaz

Molecules 2021, 26(6), 1629; https://doi.org/10.3390/molecules26061629 - 15 Mar 2021

Cited by 4 | Viewed by 2026

Abstract

Cyclic products can be obtained through the intramolecular version of the Nicholas reaction, which requires having the nucleophile connected to the alkyne unit. Here, we report the synthesis of 1-oxa-3-cyclooctynes starting from commercially available (1R,3S)-camphoric acid. The strategy is [...] Read more.

Cyclic products can be obtained through the intramolecular version of the Nicholas reaction, which requires having the nucleophile connected to the alkyne unit. Here, we report the synthesis of 1-oxa-3-cyclooctynes starting from commercially available (1R,3S)-camphoric acid. The strategy is based on the initial preparation of propargylic alcohols, complexation of the triple bond with Co₂(CO)₈, and treatment with BF₃·Et₂O to induce an intramolecular Nicholas reaction with the free hydroxyl group as nucleophile. Finally, oxidative deprotection of the alkyne afforded the cyclooctynes in good yields. Notably, large-sized R substituents at the chiral center connected to the O atom were oriented in such a way that steric interactions were minimized in the cyclization, allowing the formation of cyclooctynes exclusively with (R) configuration, in good agreement with theoretical predictions. Moreover, preliminary studies demonstrated that these cyclooctynes were reactive in the presence of azides yielding substituted triazoles. Full article

(This article belongs to the Special Issue New Synthetic Methods for Organic Compounds)

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17 pages, 4313 KiB

Open AccessArticle

Synthesis of Fluorogenic Arylureas and Amides and Their Interaction with Amines: A Competition between Turn-on Fluorescence and Organic Radicals on the Way to a Smart Label for Fish Freshness

by Javier García-Tojal, José V. Cuevas, María-Josefa Rojo, Borja Díaz de Greñu, Carla Hernando-Muñoz, José García-Calvo, Mateo M. Salgado and Tomás Torroba

Molecules 2021, 26(5), 1404; https://doi.org/10.3390/molecules26051404 - 5 Mar 2021

Cited by 2 | Viewed by 1808

Abstract

We describe the synthesis of fluorogenic arylureas and amides and their interaction with primary or secondary amines under air and light in organic-aqueous mixtures to give rise to a new class of persistent organic radicals, described on the basis of their electron paramagnetic [...] Read more.

We describe the synthesis of fluorogenic arylureas and amides and their interaction with primary or secondary amines under air and light in organic-aqueous mixtures to give rise to a new class of persistent organic radicals, described on the basis of their electron paramagnetic resonance (EPR), as well as UV–vis, fluorescence, NMR, and quantum mechanics calculations, and their prospective use as multi-signal reporters in a smart label for fish freshness. Full article

(This article belongs to the Special Issue New Synthetic Methods for Organic Compounds)

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19 pages, 2041 KiB

Open AccessArticle

Synthesis and Evaluation of Novel Iminosugars Prepared from Natural Amino Acids

by Alejandro Puet, Gema Domínguez, Francisco Javier Cañada and Javier Pérez-Castells

Molecules 2021, 26(2), 394; https://doi.org/10.3390/molecules26020394 - 13 Jan 2021

Cited by 1 | Viewed by 1873

Abstract

Cyclopropanated iminosugars have a locked conformation that may enhance the inhibitory activity and selectivity against different glycosidases. We show the synthesis of new cyclopropane-containing piperidines bearing five stereogenic centers from natural amino acids l-serine and l-alanine. Those prepared from the latter [...] Read more.

Cyclopropanated iminosugars have a locked conformation that may enhance the inhibitory activity and selectivity against different glycosidases. We show the synthesis of new cyclopropane-containing piperidines bearing five stereogenic centers from natural amino acids l-serine and l-alanine. Those prepared from the latter amino acid may mimic l-fucose, a natural-occurring monosaccharide involved in many molecular recognition events. Final compounds prepared from l-serine bear S configurations on the C5 position. The synthesis involved a stereoselective cyclopropanation reaction of an α,β-unsaturated piperidone, which was prepared through a ring-closing metathesis. The final compounds were tested as possible inhibitors of different glycosidases. The results, although, in general, with low inhibition activity, showed selectivity, depending on the compound and enzyme, and in some cases, an unexpected activity enhancement was observed. Full article

(This article belongs to the Special Issue New Synthetic Methods for Organic Compounds)

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17 pages, 990 KiB

Open AccessArticle

Synthesis, Antibacterial, and Antioxidant Evaluation of Novel Series of Condensed Thiazoloquinazoline with Pyrido, Pyrano, and Benzol Moieties as Five- and Six-Membered Heterocycle Derivatives

by Ebraheem Abdu Musad Saleh, Abdullah Mohammed AL Dawsari, Kakul Husain, Ismail Hassan Kutty and K.M.Lokanatha Rai

Molecules 2021, 26(2), 357; https://doi.org/10.3390/molecules26020357 - 12 Jan 2021

Cited by 9 | Viewed by 2320

Abstract

A novel synthesis of thiazolo[2,3-b]quinazolines 4(a–e), pyrido[2′,3′:4,5]thiazolo[2,3-b]quinazolines {5(a–e), 6(a–e), and 7(a–e)}, pyrano[2′,3′:4,5]thiazolo[2,3-b]quinazolines 8(a–e), and benzo[4,5]thiazolo[2,3-b]quinazoloine9( [...] Read more.

A novel synthesis of thiazolo[2,3-b]quinazolines 4(a–e), pyrido[2′,3′:4,5]thiazolo[2,3-b]quinazolines {5(a–e), 6(a–e), and 7(a–e)}, pyrano[2′,3′:4,5]thiazolo[2,3-b]quinazolines 8(a–e), and benzo[4,5]thiazolo[2,3-b]quinazoloine9(a–e) derivatives starting from 2-(Bis-methylsulfanyl-methylene)-5,5-dimethyl-cyclohexane-1,3-dione 2 as efficient α,α dioxoketen dithioacetal is reported and the synthetic approaches of these types of compounds will provide an innovative molecular framework to the designing of new active heterocyclic compounds. In our study, we also present optimization of the synthetic method along with a biological evaluation of these newly synthesized compounds as antioxidants and antibacterial agents against the bacterial strains, like S. aureus, E. coli, and P. aeruginosa. Among all the evaluated compounds, it was found that some showed significant antioxidant activity at 10 μg/mL while the others exhibited better antibacterial activity at 100 μg/mL. The results of this study showed that compound 6(c) possessed remarkable antibacterial activity, whereas compound 9(c) exhibited the highest efficacy as an antioxidant. The structures of the new synthetic compounds were elucidated by elemental analysis, IR, ¹H-NMR, and ¹³C-NMR. Full article

(This article belongs to the Special Issue New Synthetic Methods for Organic Compounds)

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15 pages, 3452 KiB

Open AccessArticle

Sustainable Triazine-Based Dehydro-Condensation Agents for Amide Synthesis

by Roberto Sole, Vanessa Gatto, Silvia Conca, Noemi Bardella, Andrea Morandini and Valentina Beghetto

Molecules 2021, 26(1), 191; https://doi.org/10.3390/molecules26010191 - 2 Jan 2021

Cited by 14 | Viewed by 4457

Abstract

Conventional methods employed today for the synthesis of amides often lack of economic and environmental sustainability. Triazine-derived quaternary ammonium salts, e.g., 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride (DMTMM(Cl)), emerged as promising dehydro-condensation agents for amide synthesis, although suffering of limited stability and high costs. In the present [...] Read more.

Conventional methods employed today for the synthesis of amides often lack of economic and environmental sustainability. Triazine-derived quaternary ammonium salts, e.g., 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride (DMTMM(Cl)), emerged as promising dehydro-condensation agents for amide synthesis, although suffering of limited stability and high costs. In the present work, a simple protocol for the synthesis of amides mediated by 2-chloro-4,6-dimethoxy-1,3,5-triazine (CDMT) and a tert-amine has been described and data are compared to DMTMM(Cl) and other CDMT-derived quaternary ammonium salts (DMT-Ams(X), X: Cl⁻ or ClO₄⁻). Different tert-amines (Ams) were tested for the synthesis of various DMT-Ams(Cl), but only DMTMM(Cl) could be isolated and employed for dehydro-condensation reactions, while all CDMT/tert-amine systems tested were efficient as dehydro-condensation agents. Interestingly, in best reaction conditions, CDMT and 1,4-dimethylpiperazine gave N-phenethyl benzamide in 93% yield in 15 min, with up to half the amount of tert-amine consumption. The efficiency of CDMT/tert-amine was further compared to more stable triazine quaternary ammonium salts having a perchlorate counter anion (DMT-Ams(ClO₄)). Overall CDMT/tert-amine systems appear to be a viable and more economical alternative to most dehydro-condensation agents employed today. Full article

(This article belongs to the Special Issue New Synthetic Methods for Organic Compounds)

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9 pages, 1623 KiB

Open AccessFeature PaperArticle

Multicomponent Synthesis of Luminescent Iminoboronates

by Samuel Guieu, Cátia I. C. Esteves, João Rocha and Artur M. S. Silva

Molecules 2020, 25(24), 6039; https://doi.org/10.3390/molecules25246039 - 21 Dec 2020

Cited by 4 | Viewed by 2390

Abstract

A family of iminoboronates was prepared through a one-pot multicomponent reaction, starting from boronic acid, anthranilic acid, and different salicylaldehydes. Their synthesis was straightforward and the complexes were obtained in good to excellent yields. Their photophysical properties were assessed in a diluted solution, [...] Read more.

A family of iminoboronates was prepared through a one-pot multicomponent reaction, starting from boronic acid, anthranilic acid, and different salicylaldehydes. Their synthesis was straightforward and the complexes were obtained in good to excellent yields. Their photophysical properties were assessed in a diluted solution, and the complexes proved to be faintly luminescent. These chelates demonstrated remarkable Aggregation-Induced Emission Enhancement, which was rationalized using crystal structures. Full article

(This article belongs to the Special Issue New Synthetic Methods for Organic Compounds)

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17 pages, 8206 KiB

Open AccessFeature PaperArticle

Sustainable Access to Acridin-9-(10H)ones with an Embedded m-Terphenyl Moiety Based on a Three-Component Reaction

by Damiano Rocchi, Jorge Gómez-Carpintero, Juan F. González and J. Carlos Menéndez

Molecules 2020, 25(23), 5565; https://doi.org/10.3390/molecules25235565 - 27 Nov 2020

Cited by 1 | Viewed by 2066

Abstract

A Ce(IV)-catalyzed three-component reaction between chalcones, anilines and β-ketoesters followed by a microwave-assisted thermal cyclization afforded 1,3-diaryl-1,2-dihydroacridin-9(10H)-ones. Their microwave irradiation in nitrobenzene, acting both as solvent and oxidant, afforded fully unsaturated 1,3-diarylacridin-9(10H)-ones, which combine acridin-9-(10H)one and m [...] Read more.

A Ce(IV)-catalyzed three-component reaction between chalcones, anilines and β-ketoesters followed by a microwave-assisted thermal cyclization afforded 1,3-diaryl-1,2-dihydroacridin-9(10H)-ones. Their microwave irradiation in nitrobenzene, acting both as solvent and oxidant, afforded fully unsaturated 1,3-diarylacridin-9(10H)-ones, which combine acridin-9-(10H)one and m-terphenyl moieties. Overall, the route generates three C-C and one C-N bond and has the advantage of requiring a single chromatographic separation. Full article

(This article belongs to the Special Issue New Synthetic Methods for Organic Compounds)

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14 pages, 2775 KiB

Open AccessArticle

Ethyne Functionalized Meso-Phenothiazinyl-Phenyl-Porphyrins: Synthesis and Optical Properties of Free Base Versus Protonated Species

by Eva Molnar, Emese Gál, Luiza Găină, Castelia Cristea and Luminița Silaghi-Dumitrescu

Molecules 2020, 25(19), 4546; https://doi.org/10.3390/molecules25194546 - 4 Oct 2020

Cited by 3 | Viewed by 2239

Abstract

Synthesis, structural characterization and photophysical properties for a series of new trans-A₂B₂- and A₃B-type ethynyl functionalized meso-phenothiazinyl-phenyl porphyrin derivatives are described. The new compounds displayed the characteristic porphyrin absorption spectra slightly modified by weak auxochromic [...] Read more.

Synthesis, structural characterization and photophysical properties for a series of new trans-A₂B₂- and A₃B-type ethynyl functionalized meso-phenothiazinyl-phenyl porphyrin derivatives are described. The new compounds displayed the characteristic porphyrin absorption spectra slightly modified by weak auxochromic effects of the substituents and fluorescence emission in the range of 651–659 nm with 11–25% quantum yields. The changes recorded in the UV-vis absorption spectra in the presence of trifluoroacetic acid (TFA) are consistent with the protonation of the two internal nitrogen atoms of the free-base porphyrin (19 nm bathochromic shift of the strong Soret band and one long wave absorption maxima situated in the range of 665–695 nm). Protonation of the phenothiazine substituents required increased amounts of TFA and produced a distinct hypsochromic shift of the long wave absorption maxima. The density functional theory (DFT) calculations of a porphyrin dication pointed out a saddle-distorted porphyrin ring as the ground-state geometry. Full article

(This article belongs to the Special Issue New Synthetic Methods for Organic Compounds)

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13 pages, 6942 KiB

Open AccessArticle

Exploring the Scope of Tandem Palladium and Isothiourea Relay Catalysis for the Synthesis of α-Amino Acid Derivatives

by Jacqueline Bitai, Alexandra M. Z. Slawin, David B. Cordes and Andrew D. Smith

Molecules 2020, 25(10), 2463; https://doi.org/10.3390/molecules25102463 - 25 May 2020

Cited by 6 | Viewed by 3775

Abstract

The scope and limitations of a tandem N-allylation/[2,3]-rearrangement protocol are investigated through the incorporation of a variety of functional groups within an allylic phosphate precursor. This method uses readily accessible N,N-dimethylglycine aryl esters and functionalized allylic phosphates, forming quaternary ammonium salts in situ [...] Read more.

The scope and limitations of a tandem N-allylation/[2,3]-rearrangement protocol are investigated through the incorporation of a variety of functional groups within an allylic phosphate precursor. This method uses readily accessible N,N-dimethylglycine aryl esters and functionalized allylic phosphates, forming quaternary ammonium salts in situ in the presence of a palladium catalyst. Subsequent enantioselective [2,3]-sigmatropic rearrangement, promoted by the chiral isothiourea tetramisole, generates α-amino acid derivatives with two contiguous stereocenters. The incorporation of electron-withdrawing ester and amide groups gave the best results, furnishing the desired products in moderate to good yields (29–70%), with low diastereocontrol (typically 60:40 dr) but high enantioselectivity (up to 90:10 er). These results indicate that substrate–catalyst interactions in the proposed transition state are sensitive to the substitution pattern of the substrates. Full article

(This article belongs to the Special Issue New Synthetic Methods for Organic Compounds)

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13 pages, 1317 KiB

Open AccessArticle

Copper-Promoted One-Pot Approach: Synthesis of Benzimidazoles

by S. N. Murthy Boddapati, Ramana Tamminana, Ravi Kumar Gollapudi, Sharmila Nurbasha, Mohamed E. Assal, Osamah Alduhaish, Mohammed Rafiq H. Siddiqui, Hari Babu Bollikolla and Syed Farooq Adil

Molecules 2020, 25(8), 1788; https://doi.org/10.3390/molecules25081788 - 14 Apr 2020

Cited by 18 | Viewed by 3898

Abstract

A facile, one-pot, and proficient method was developed for the production of various 2-arylaminobenzimidazoles. This methodology is based for the first time on a copper catalyst promoted domino C–N cross-coupling reaction for the generation of 2-arylaminobenzimidazoles. Mechanistic investigations revealed that the synthetic pathway [...] Read more.

A facile, one-pot, and proficient method was developed for the production of various 2-arylaminobenzimidazoles. This methodology is based for the first time on a copper catalyst promoted domino C–N cross-coupling reaction for the generation of 2-arylaminobenzimidazoles. Mechanistic investigations revealed that the synthetic pathway involves a copper-based desulphurization/nucleophilic substitution and a subsequent domino intra and intermolecular C–N cross-coupling reactions. Some of the issues typically encountered during the synthesis of 2-arylaminobezimidazoles, including the use of expensive catalytic systems and the low reactivity of bromo precursors, were addressed using this newly developed copper-catalyzed method. The reaction procedure is simple, generally with excellent substrate tolerance, and provides good to high yields of the desired products. Full article

(This article belongs to the Special Issue New Synthetic Methods for Organic Compounds)

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9 pages, 1719 KiB

Open AccessCommunication

Regioselective Monobromination of Phenols with KBr and ZnAl–BrO₃⁻–Layered Double Hydroxides

by Ligeng Wang, Chun Feng, Yan Zhang and Jun Hu

Molecules 2020, 25(4), 914; https://doi.org/10.3390/molecules25040914 - 18 Feb 2020

Cited by 4 | Viewed by 7110

Abstract

The regioselective mono-bromination of phenols has been successfully developed with KBr and ZnAl–BrO₃⁻–layered double hydroxides (abbreviated as ZnAl–BrO₃⁻–LDHs) as brominating reagents. The para site is much favorable and the ortho site takes the priority if para site [...] Read more.

The regioselective mono-bromination of phenols has been successfully developed with KBr and ZnAl–BrO₃⁻–layered double hydroxides (abbreviated as ZnAl–BrO₃⁻–LDHs) as brominating reagents. The para site is much favorable and the ortho site takes the priority if para site is occupied. This reaction featured with excellent regioselectivity, cheap brominating reagents, mild reaction condition, high atom economy, broad substrate scope, and provided an efficient method to synthesize bromophenols. Full article

(This article belongs to the Special Issue New Synthetic Methods for Organic Compounds)

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13 pages, 6039 KiB

Open AccessArticle

Unexpected Rearrangement of N-Allyl-2-phenyl-4,5-Dihydrooxazole-4-Carboxamides to Construct Aza-Quaternary Carbon Centers

by Goyeong Choi, Seoyoung Jo, Juyeon Mun, Yonguk Jeong, Seok-Ho Kim and Jong-Wha Jung

Molecules 2019, 24(24), 4495; https://doi.org/10.3390/molecules24244495 - 8 Dec 2019

Cited by 2 | Viewed by 3723

Abstract

The unexpected rearrangement of N-allyl-2-phenyl-4,5-dihydrooxazole-4-carboxamides in the presence of LiHMDS has been found. The key features are: (1) the net reaction consisted of 1,3-migration of the N-allyl group, (2) the rearrangement produced a congested aza-quaternary carbon center, (3) both cyclic and [...] Read more.

The unexpected rearrangement of N-allyl-2-phenyl-4,5-dihydrooxazole-4-carboxamides in the presence of LiHMDS has been found. The key features are: (1) the net reaction consisted of 1,3-migration of the N-allyl group, (2) the rearrangement produced a congested aza-quaternary carbon center, (3) both cyclic and acyclic substrates underwent the unexpected rearrangement to afford products in moderate to high yields, and (4) the reaction seemed to be highly stereoselective. In addition, a plausible mechanism has been discussed. Full article

(This article belongs to the Special Issue New Synthetic Methods for Organic Compounds)

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8 pages, 691 KiB

Open AccessArticle

A New Alkylation of Aryl Alcohols by Boron Trifluoride Etherate

by Ndze Denis Jumbam, Yamkela Maganga, Wayiza Masamba, Nomthandazo I. Mbunye, Esethu Mgoqi and Sphumusa Mtwa

Molecules 2019, 24(20), 3720; https://doi.org/10.3390/molecules24203720 - 16 Oct 2019

Cited by 3 | Viewed by 6566

Abstract

The ethylation of aryl alcohols by an ethyl moiety of boron trifluoride etherate is described. The reaction proceeded cleanly and afforded good yields of the corresponding aryl ethyl ethers. It tolerated the presence of functional groups such as aryl, alkyl, halogens, nitro, nitrile, [...] Read more.

The ethylation of aryl alcohols by an ethyl moiety of boron trifluoride etherate is described. The reaction proceeded cleanly and afforded good yields of the corresponding aryl ethyl ethers. It tolerated the presence of functional groups such as aryl, alkyl, halogens, nitro, nitrile, and amino. However, the presence of amino or nitro groups ortho to a hydroxyl group of an aryl compound drastically reduced the yields of the anticipated products due to the chelation of the aforementioned functional groups with boron trifluoride etherate. A nitrogen atom in the aromatic ring system, as exemplified by hydroxypyridine and 8-hydroxyquinoline, completely inhibited the reaction. Resorcinol, hydroquinone, and aryl alcohols with aldehyde functions decomposed under the reaction conditions. Full article

(This article belongs to the Special Issue New Synthetic Methods for Organic Compounds)

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Review

Jump to: Research

32 pages, 12661 KiB

Open AccessReview

1,3-Cyclohexadien-1-Als: Synthesis, Reactivity and Bioactivities

by Ignacio E. Tobal, Rocío Bautista, David Diez, Narciso M. Garrido and Pilar García-García

Molecules 2021, 26(6), 1772; https://doi.org/10.3390/molecules26061772 - 22 Mar 2021

Cited by 2 | Viewed by 3101

Abstract

In synthetic organic chemistry, there are very useful basic compounds known as building blocks. One of the main reactions wherein they are applied for the synthesis of complex molecules is the Diels–Alder cycloaddition. This reaction is between a diene and a dienophile. Among [...] Read more.

In synthetic organic chemistry, there are very useful basic compounds known as building blocks. One of the main reactions wherein they are applied for the synthesis of complex molecules is the Diels–Alder cycloaddition. This reaction is between a diene and a dienophile. Among the most important dienes are the cyclic dienes, as they facilitate the reaction. This review considers the synthesis and reactivity of one of these dienes with special characteristics—it is cyclic and has an electron withdrawing group. This building block has been used for the synthesis of biologically active compounds and is present in natural compounds with interesting properties. Full article

(This article belongs to the Special Issue New Synthetic Methods for Organic Compounds)

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40 pages, 33265 KiB

Open AccessReview

Modern Synthetic Methods for the Stereoselective Construction of 1,3-Dienes

by Raquel G. Soengas and Humberto Rodríguez-Solla

Molecules 2021, 26(2), 249; https://doi.org/10.3390/molecules26020249 - 6 Jan 2021

Cited by 43 | Viewed by 5481

Abstract

The 1,3-butadiene motif is widely found in many natural products and drug candidates with relevant biological activities. Moreover, dienes are important targets for synthetic chemists, due to their ability to give access to a wide range of functional group transformations, including a broad [...] Read more.

The 1,3-butadiene motif is widely found in many natural products and drug candidates with relevant biological activities. Moreover, dienes are important targets for synthetic chemists, due to their ability to give access to a wide range of functional group transformations, including a broad range of C-C bond-forming processes. Therefore, the stereoselective preparation of dienes have attracted much attention over the past decades, and the search for new synthetic protocols continues unabated. The aim of this review is to give an overview of the diverse methodologies that have emerged in the last decade, with a focus on the synthetic processes that meet the requirements of efficiency and sustainability of modern organic chemistry. Full article

(This article belongs to the Special Issue New Synthetic Methods for Organic Compounds)

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