Convenient Synthesis of the Branched Hexasaccharide Repeating Unit of the Cell Wall O-Antigen of Escherichia coli O80 Strain
Synthesis DOI: 10.1055/s-0043-1763649 Chemical synthesis of a branched hexasaccharide corresponding to the cell wall O-antigen of Escherichia coli (E. coli) O80 strain has been achieved in very good yield with satisfactory stereochemical outcome around the glycosidic linkages by applying a regio- and stereoselective [4+2] block glycosylation strategy. The tetrasaccharide diol derivative was synthesized from suitably functionalized monosaccharide intermediates using sequential stereoselective glycosylations and the disaccharide thioglycoside donor was obtained applying a regio- and stereoselective orthogonal armed-disarmed ...
Source: Synthesis - December 11, 2023 Category: Chemistry Authors: Sahaji, Samim Misra, Anup Kumar Tags: paper Source Type: research
Metal-Free Synthesis of 9-Sulfenylphenanthrenes via HNO3/HCl-Promoted Annulation of 2-Alkynylbiaryls with Disulfides
Synthesis DOI: 10.1055/a-2204-8461 A metal-free thiolative annulation of 2-alkynylbiaryls with disulfides has been developed. This mild and efficient approach was promoted by inexpensive HNO3/HCl and afforded a range of corresponding 9-sulfenylphenanthrenes in good to excellent yields with a broad substrate scope and high functional group tolerance. Both sulfide groups of the disulfide reagent were used in the reaction. [...] Georg Thieme Verlag KG Rüdigerstraße 14, 70469 Stuttgart, GermanyArticle in Thieme eJournals: Table of contents | Abstract | Full text (Source: Synthesis)
Source: Synthesis - December 11, 2023 Category: Chemistry Authors: Luan, Tian Huang, Xiao-Cheng Yao, Zhi-Xiang Su, Hui Yu, Wan-Guo Tags: paper Source Type: research
Synthesis of Novel Enantiopure Amino- and Azidopyran Building Blocks and Their Click Reactions to Multivalent Carbohydrate Mimetics
Synthesis DOI: 10.1055/s-0043-1763619 The synthesis of three enantiopure 1,2-oxazine-derived azides was optimized and the reductions of these compounds to amino alcohols were studied. As a primary aim of this study, the copper-catalyzed (3+2)-cycloadditions of the azides were investigated, employing a series of alkynes, dialkynes, and trialkynes, which afforded the corresponding mono-, di-, and trivalent triazole derivatives with different rigid and flexible core elements. The expected click products were generally obtained in good to excellent yields when copper iodide was employed in presence of tris[(1-benzyl-1H-1,2,3-t...
Source: Synthesis - December 6, 2023 Category: Chemistry Authors: Ko óš, Peter Reissig, Hans-Ulrich Tags: paper Source Type: research
Novel Two-Step Synthesis of N-Alkylated 2,3-Diaryl-4-quinolones
Synthesis DOI: 10.1055/s-0042-1751530 A library of 18 polysubstituted 4-quinolones was conveniently prepared via simple and practical protocol involving N-alkylation of 2-(3-oxoindolin-2-yl)acetonitriles and following NaH-induced ring expansion. The current two-step approach provides feasible access to a subclass of N-protected C3-aryl-substituted 2-phenyl-4-quinolones starting with or just one step away from commercially available 2-arylindoles and nitrostyrenes. [...] Georg Thieme Verlag KG Rüdigerstraße 14, 70469 Stuttgart, GermanyArticle in Thieme eJournals: Table of contents | Abstract | Full text (Source: Synthesis)
Source: Synthesis - December 6, 2023 Category: Chemistry Authors: Aksenov, Alexander V. Arutiunov, Nikolai A. Zatsepilina, Anna M. Aksenova, Anna A. Aleksandrova, Elena V. Aksenov, Nicolai A. Leontiev, Alexander V. Aksenov, Dmitrii A. Tags: paper Source Type: research
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Synthesis 2024; 56: V- DOI: 10.1055/s-0040-1720101 Georg Thieme Verlag KG Rüdigerstraße 14, 70469 Stuttgart, GermanyArticle in Thieme eJournals: Table of contents (Source: Synthesis)
Source: Synthesis - December 6, 2023 Category: Chemistry Tags: table of contents Source Type: research
A Formal Exchange Reaction between Ketones and Vinyl Ethers with Solid Catalysts
Synthesis DOI: 10.1055/a-2204-2801 The formal exchange of functional groups in internal positions of two different molecules is of interest in synthetic chemistry, as a simple retrosynthetic strategy. Here the formal exchange reaction between internal α-methylene ketones and vinyl ethers, retaining the original C–O bonds is presented. This process offers a new route for the synthesis of vinyl ethers in one step from ketones, including 1,3-diketones, under mild reaction conditions. Besides, the reaction is catalyzed by reusable cheap solids and can be carried out in flow for 20 days without signs of catalyst depletion. C...
Source: Synthesis - December 5, 2023 Category: Chemistry Authors: Mingueza-Verdejo, Paloma Cer ón-Carrasco, Jose Pedro Oliver-Meseguer, Judit Leyva-P érez, Antonio Tags: paper Source Type: research
Phosphine Ligand Effects in Nickel-Catalyzed Alkene Migratory Hydroalkylation
Synthesis DOI: 10.1055/a-2204-8921 Catalytic alkene hydroalkylation has provided to be an efficient method for synthesizing C(sp3) centers, from readily available and inexpensive alkene starting materials through alkene hydrometallation followed by cross-coupling. One of the major tasks in this field is to develop diverse ligands to achieve regioselective control. Herein, we report the investigation of nickel–triphenylphosphine-catalyzed remote hydroalkylation of alkenyl amides to access α-branched amines. Various alkenes and alkyl iodides are suitable substrates to deliver the desired products with excellent regioselec...
Source: Synthesis - December 4, 2023 Category: Chemistry Authors: Zhu, Qing-Wei Liu, Deguang Li, Zhen Wang, Jia-Wang Nie, Wan Lu, Xi Fu, Yao Tags: paper Source Type: research
Total Synthesis of Lucidumone: Attempted Shortcuts, Dead Ends and Lessons Learnt
Synthesis DOI: 10.1055/s-0042-1751529 Lucidumone is a meroterpenoid isolated from the mushroom Ganoderma lucidum, displaying selective COX-2 inhibitory activity. In this work, we detail our synthetic efforts which led to the first enantioselective synthesis of lucidumone in 13 steps (longest linear sequence). Beyond the key retro-[4+2]/intramolecular Diels–Alder cascade, we discuss the difficulties regarding fragment assembly, introduction of the methyl ketone moiety and choice of adequate protecting group. [...] Georg Thieme Verlag KG Rüdigerstraße 14, 70469 Stuttgart, GermanyArticle in Thieme eJournals: Table of cont...
Source: Synthesis - December 4, 2023 Category: Chemistry Authors: Huang, Guangho Laporte, Amaury Pag ès, Lucas Kouklovsky, Cyrille de la Torre, Aur élien Tags: paper Source Type: research
Base-Catalyzed Deprotection of Aldehydes: A New Haloform Reaction
Synthesis DOI: 10.1055/a-2201-3503 An efficient procedure for the deprotection of α,α,α-trihalogen (Cl, Br) methyl alcohols under mild reaction conditions to produce the corresponding aldehydes and haloforms is described. This method can be applied to the deprotection of aromatic, aliphatic, and heterocyclic trihalomethyl alcohol compounds. [...] Georg Thieme Verlag KG Rüdigerstraße 14, 70469 Stuttgart, GermanyArticle in Thieme eJournals: Table of contents | Abstract | Full text (Source: Synthesis)
Source: Synthesis - December 4, 2023 Category: Chemistry Authors: Abulipizi, Gulizhabaier Abuduwaili, Kadierya Tian, Shiying Maihemuti, Mailikezhati Abulikemu, Abudu Rexit Tags: paper Source Type: research
N-Oxide Route to the Marine Natural Product Cyanogramide D
Synthesis DOI: 10.1055/a-2202-7145 The first synthesis of the marine natural product cyanogramide D is reported. The key step is the acetylation of a β-carboline N-oxide, followed by acetyl migration. Since in this particular case it was not possible to incorporate the styryl side chain by Buchwald coupling, a phenylethanolamine side chain was attached, which was dehydrated with Martin’s sulfurane after assembly of the tetracycle. Pentacyclic products were obtained under Appel conditions. The synthesis will facilitate the exploration of the biomimetic oxidative spirocyclization of cyanogramide D to the spirooxindole c...
Source: Synthesis - December 4, 2023 Category: Chemistry Authors: Sarnes, Dustin M. Struck, Valentina Jones, Peter G. Lindel, Thomas Tags: feature Source Type: research
Carboxamide-Accelerated Chemoselective Borylation of Iodoarenes under Photoirradiation
This study reports on the ortho-specific and chemoselective borylation of ortho-iodoarene possessing carboxamide under visible-light irradiation. When a haloarene containing both C–I and C–X bonds is employed as a substrate, another C–X bond (not ortho) remains intact during the reaction. Mechanistic studies revealed that the key to the success of this reaction is the generation of a diboron-bridged five-membered ring as a transition state, in which the diboron-bridged five-membered ring and the benzene ring in the transition state are perpendicular to each other, owing to steric repulsion by the iodine atom at the o...
Source: Synthesis - November 30, 2023 Category: Chemistry Authors: Nakashima, Yusei Sumimoto, Michinori Nishikata, Takashi Tags: paper Source Type: research
Synthesis of Piperazin-2-one Derivatives via Cascade Double Nucleophilic Substitution
Synthesis DOI: 10.1055/a-2201-9951 A cascade, metal-promoted transformation utilizing chloro allenylamide, primary amine, and aryl iodide afforded piperizinones in good yields. Under the optimized conditions the cascade is performed as a one-pot process allowing the formation of three bonds. The synthetic route, controlled by the reaction rates of several processes involved, introduces two points of diversity and is well suited for combinatorial synthesis or related technologies. [...] Georg Thieme Verlag KG Rüdigerstraße 14, 70469 Stuttgart, GermanyArticle in Thieme eJournals: Table of contents | Abstract | ...
Source: Synthesis - November 29, 2023 Category: Chemistry Authors: Petkovic, Milos Kusljevic, Du šica Jovanovic, Milos Jovanovic, Predrag Tasic, Gordana Simic, Milena Savic, Vladimir Tags: paper Source Type: research
A Convergent Approach for the Synthesis of C14 –C26 Fragment of Anticancer Drug Eribulin Mesylate
Synthesis DOI: 10.1055/a-2202-5597 The stereoselective synthesis of C14–C26 fragment of eribulin is reported in a convergent way by coupling of fragment C14–C19 with fragment C20–C26 that are accessible from commercially available raw materials crotonic acid and 1,4-butanediol. The key steps involved in this practical approach are Hosomi–Sakurai asymmetric alkylation, Maruoka allylation, Noyori reduction, silver-catalyzed one-pot rearrangement, and intramolecular cyclization. [...] Georg Thieme Verlag KG Rüdigerstraße 14, 70469 Stuttgart, GermanyArticle in Thieme eJournals: Table of contents | Abstract |...
Source: Synthesis - November 29, 2023 Category: Chemistry Authors: Nasam, Rajesh Pabbaraja, Srihari Tags: paper Source Type: research
Efficient Synthesis of (Z)-4-((Substituted phenylamino)methyl idene)isoquinoline-1,3(2H,4H)-diones Using the Eschenmoser Coupling Reaction
Synthesis DOI: 10.1055/a-2198-1589 A novel synthetic strategy involving the Eschenmoser coupling reaction of 4-bromoisoquinoline-1,3(2H,4H)-diones with substituted thioformanilides, thioacetanilides, and thiobenzanilides gave 18 (Z)-4-((substituted phenylamino)methylidene)isoquinoline-1,3(2H,4H)-diones. The reaction occurs under mild conditions (DMF or MeCN, 25–60 °C) without any base or thiophile and in good yields (43–95%). Furthermore, for the synthesis of starting thioformanilides carrying basic substituents, a new thioacylation protocol was developed that involves a thioacylating agent formed from carbon disulfid...
Source: Synthesis - November 29, 2023 Category: Chemistry Authors: Marek, Luk áš V áňa, Jiří Svoboda, Jan Svobodov á, Markéta Hanusek, Ji ří Tags: paper Source Type: research
Pyrazolopyridine Ligands in Transition-Metal-Catalyzed C –C and C–Heteroatom Bond-Forming Reactions
Conclusion [...] Georg Thieme Verlag KG Rüdigerstraße 14, 70469 Stuttgart, GermanyArticle in Thieme eJournals: Table of contents | Abstract | Full text (Source: Synthesis)
Source: Synthesis - November 28, 2023 Category: Chemistry Authors: Kang, Eunsu Joo, Jung Min Tags: short review Source Type: research
