Domino Ring Expansion: Regioselective Access to 9-Membered Lactones with a Fused Indole Unit from 2-Nitrophenyl-1,3-cyclohexanediones.

No abstract is available for this paper.

• Publication year

  2018

• Venue

  Chemistry

• Publication date

  2018-02-09

• Fields of study

  Medicine, Chemistry

• Identifiers
  DOI 10.1002/chem.201705645PMID 29286174
• External record

  Open on Semantic Scholar

• Source metadata

  Semantic Scholar, PubMed

• No claims are published for this paper.

• No concepts are published for this paper.

• Iterative Assembly of Macrocyclic Lactones using Successive Ring Expansion Reactions

  2018cited by this paper
• Synthesis of Benzannulated Medium-ring Lactams via a Tandem Oxidative Dearomatization-Ring Expansion Reaction.

  2018cited by this paper
• One-Pot Assembly of Amino Acid Bridged Hybrid Macromulticyclic Cages through Multiple Multicomponent Macrocyclizations.

  2017cited by this paper
• Design and Enantioselective Construction of Axially Chiral Naphthyl-Indole Skeletons.

  2017cited by this paper
• Remote C6-Selective Ruthenium-Catalyzed C–H Alkylation of Indole Derivatives via σ-Activation

  2017cited by this paper
• Construction of Nine-Membered Heterocycles through Palladium-Catalyzed Formal [5+4] Cycloaddition.

  2017cited by this paper
• Synthesis of 2,3‐Disubstituted Indoles from α‐Diketones and N‐Substituted Anilines: One‐Pot Pd‐Catalyzed Reductive Amination

  2017cited by this paper
• Ring-Expansion Approach to Medium-Sized Lactams and Analysis of Their Medicinal Lead-Like Properties.

  2017cited by this paper
• N-Heterocyclic carbene (NHC)-catalysed atom economical construction of 2,3-disubstituted indoles.

  2017cited by this paper
• Indole Synthesis via Cyclative Formation of 2,3-Dizincioindoles and Regioselective Electrophilic Trapping.

  2017cited by this paper
• N-Heterocyclic-Carbene-Catalyzed Umpolung of Imines.

  2017cited by this paper
• Palladium Catalyzed Asymmetric Three-Component Coupling of Boronic Esters, Indoles, and Allylic Acetates.

  2017cited by this paper
• Ring-Expansion Reactions in the Synthesis of Macrocycles and Medium-Sized Rings.

  2017cited by this paper
• Radical aryl migration enables diversity-oriented synthesis of structurally diverse medium/macro- or bridged-rings

  2016cited by this paper
• Concise Total Syntheses of (+)-Haplocidine and (+)-Haplocine via Late-Stage Oxidation of (+)-Fendleridine Derivatives.

  2016cited by this paper
• Medium-Ring Nitrogen Heterocycles through Migratory Ring Expansion of Metalated Ureas.

  2016cited by this paper
• Concise Synthesis of a Pateamine A Analogue with In Vivo Anticancer Activity Based on an Iron-Catalyzed Pyrone Ring Opening/Cross-Coupling.

  2016cited by this paper
• An expedient strategy for the diversity-oriented synthesis of macrocyclic compounds with natural product-like characteristics

  2016cited by this paper
• Kinetic or Dynamic Control on a Bifurcating Potential Energy Surface? An Experimental and DFT Study of Gold-Catalyzed Ring Expansion and Spirocyclization of 2-Propargyl-β-tetrahydrocarbolines.

  2015cited by this paper
• The Synthesis of Structurally Diverse Macrocycles By Successive Ring Expansion.

  2015cited by this paper
• Enantioselective Synthesis of Medium‐Sized‐Ring Lactones by Organocatalytic Michael Addition Followed by Reductively Initiated Fragmentation

  2015cited by this paper
• Synthesis of tetrahydropyran/tetrahydrofuran-containing macrolides by palladium-catalyzed alkoxycarbonylative macrolactonizations.

  2014cited by this paper
• The Witkop cyclization: a photoinduced C-H activation of the indole system.

  2014cited by this paper
• Die Witkop‐Cyclisierung: eine photoinduzierte C‐H‐Aktivierung des Indolsystems

  2014cited by this paper
• Gated access to α-lithiated phenyltetrahydrofuran: functionalisation via direct lithiation of the parent oxygen heterocycle.

  2013cited by this paper
• Alkinmetathese im Aufwind

  2013cited by this paper
• Alkyne metathesis on the rise.

  2013cited by this paper
• Synthesis of eight-membered lactones: intermolecular [6+2] cyclization of amphoteric molecules with siloxy alkynes.

  2012cited by this paper
• Efficient medium ring size bromolactonization using a sulfur-based zwitterionic organocatalyst.

  2012cited by this paper
• Domino alkylation/oxa-Michael of 1,3-cyclohexanediones: steering the C/O-chemoselectivity to reach tetrahydrobenzofuranones.

  2011cited by this paper
• Total synthesis of aspergillide A and B based on the transannular oxy-Michael reaction.

  2011cited by this paper
• Highly efficient synthesis of medium-sized lactones via oxidative lactonization: concise total synthesis of isolaurepan.

  2010cited by this paper
• Metathesis in Natural Product Synthesis: Strategies, Substrates and Catalysts

  2010cited by this paper
• Total Synthesis of (±)‐Quebrachamine via [3+2] Cycloaddition and Efficient Chloroacetamide Photocyclization

  2009cited by this paper
• Ruthenium-based olefin metathesis catalysts bearing N-heterocyclic carbene ligands.

  2009cited by this paper
• Domino double Michael-Claisen cyclizations: a powerful general tool for introducing quaternary stereocenters at C4 of cyclohexane-1,3-diones and total synthesis of diverse families of sterically congested alkaloids.

  2008cited by this paper
• Total synthesis of natural 8- and 9-membered lactones: recent advancements in medium-sized ring formation.

  2007cited by this paper
• Improved biomimetic total synthesis of D,L-stephacidin A.

  2007cited by this paper
• Cyclopentanone ring expansion leading to functionalized delta-lactams: short synthesis of simple sedum alkaloids.

  2007cited by this paper
• Macrolactonizations in the total synthesis of natural products.

  2006cited by this paper
• Macrolactonization via hydrocarbon oxidation.

  2006cited by this paper
• A novel tunable aromatic bromination method using alkyl bromides and sodium hydride in DMSO

  2006cited by this paper
• New silicon-mediated, sequential ring expansions of n-sized 2-cycloalkenones into hydroxyolefinic n + m + p medium-sized lactones: short synthesis of (-)-phoracantholide-J.

  2005cited by this paper
• Handbook of metathesis

  2003cited by this paper
• New silicon-mediated ring expansion of n-sized conjugated cycloalkenones into homoallylic n+3 lactones

  2003cited by this paper
• Cerium(III) chloride promoted highly regioselective ring opening of epoxides and aziridines using NaN(3) in acetonitrile: a facile synthesis of 1,2-azidoalcohols and 1,2-azidoamines.

  2002cited by this paper
• Revisiting [3 + 3] route to 1,3-cyclohexanedione frameworks: hidden aspect of thermodynamically controlled enolates.

  2001cited by this paper
• C-C versus C-O anionic domino cycloalkylation of stabilized carbanions: facile one-pot stereoselective preparation of functionalized bridged bicycloalkanones and cyclic enol ethers.

  2001cited by this paper
• Totalsynthese von (−)‐Strychnin über den Wieland‐Gumlich‐Aldehyd

  1999cited by this paper
• Total Synthesis of (-)-Strychnine via the Wieland-Gumlich Aldehyde.

  1999cited by this paper
• Synthesis and oxidative fragmentation of catharanthine analogs. Comparison to the fragmentation — Coupling of catharanthine and vindoline

  1998cited by this paper
• The Olefin Metathesis Approach to Epothilone A and Its Analogues

  1997cited by this paper
• Total Synthesis of (−)‐Epothilone A

  1997cited by this paper
• AN ENANTIOSELECTIVE SYNTHESIS OF THE STRYCHNOS ALKALOID (-)-TUBIFOLINE

  1996cited by this paper
• Domino Reactions in Organic Synthesis.

  1996cited by this paper
• 3a-(o-Nitrophenyl)octahydroindol-4-ones: Synthesis and spectroscopic analysis

  1996cited by this paper
• Medium ring lactones

  1995cited by this paper
• A Concise Method for Stereocontrolled Preparation of Medium-Sized Lactones

  1995cited by this paper
• Studies on the Synthesis of Strychnos Indole Alkaloids. Synthesis of (.+-.)-Dehydrotubifoline

  1995cited by this paper
• Cascade Catalysis in Synthesis. An Enantioselective Route to Sch 38516 (and Fluvirucin B1) Aglycon Macrolactam

  1995cited by this paper
• Syntheses of Medium Sized Rings by Ring Expansion Reactions

  1994cited by this paper
• A new, general synthetic pathway to Strychnos indole alkaloids. First total synthesis of (.+-.)-echitamidine

  1993cited by this paper
• A new synthesis of medium ring and macrocyclic acetylenic lactones from oxabicycloalkenones via their tosylhydrazones

  1993cited by this paper
• Use of metal complexation in the synthesis of medium-ring acetylenic lactones

  1992cited by this paper
• Synthesis of 3,3-Dimethyl-5-oxo-6-alkyloctanolides by Ring Expansion of Appropriately Substituted Cyclohexane-1,3-diones

  1990cited by this paper
• Synthesis of vinca alkaloids and related compounds XLVIII synthesis of (+)-catharanthine and (±)-allocatharanthine

  1990cited by this paper
• One-pot, four-component annulations: flexible and simple syntheses of unsaturated macrolides and of substituted aromatics and heteroaromatics

  1988cited by this paper
• New general synthesis of medium ring-lactones via a regioselective β-scission of alkoxyl radicals generated from catacondensed lactols

  1987cited by this paper
• A new synthesis of medium, and large membered lactones via denitration of nitro-lactones

  1984cited by this paper
• Synthesen makrocyclischer Lactone durch Ringerweiterung Herstellung von (±)‐Phoracantholid I, (±)‐Dihydrorecifeiolid und (±)‐15‐Hexadecanolid

  1984cited by this paper
• Young Pharmacists Award

  1982cited by this paper
• A new synthesis of macrocyclic keto-lactones via ring expansion of 2-(3-hydroxypropyl)-2-nitrocycloalkanones

  1982cited by this paper
• A new synthesis of macrocyclic lactones by rearrangement of 2-hydroxyalkyl-2-phenylsulphonylcycloalkanones

  1981cited by this paper
• Synthese de macrolides par methathese.

  1980cited by this paper
• Die “Zip”-Reaktion: Eine neue Methode zur Ringerweiterung; Synthese von 17- und 21gliedrigen Polyaminolactamen

  1977cited by this paper
• The “Zip” Reaction: A New Method for Ring Expansion; Synthesis of 17‐ and 21‐ Membered Polyaminolactams

  1977cited by this paper
• Novel Synthesis of Ketolactones by Intramolecular Reverse Dieckmann Reaction1

  1976cited by this paper
• Photocyclization of 2-(N-chloroacetylpiperidylalkyl)indoles. Novel case of stereoisomerism dependent on sterically restrained conformations

  1975cited by this paper
• A new synthesis of a stemmadenine model

  1975cited by this paper
• Photocyclization of 2-Indolylalkyl N-Chloroacetamides1,2

  1975cited by this paper

• Modular Assembly of Macrocyclic Sulfonamides via Consecutive Cascade Ring Expansion Reactions.

  2025cites this paper
• Stereoselective synthesis of atropisomeric amides enabled by intramolecular acyl transfer

  2025cites this paper
• A Modular Strategy for the Synthesis of Macrocycles and Medium-Sized Rings via Cyclization/Ring Expansion Cascade Reactions

  2024cites this paper
• Cascade ring expansion reactions for the synthesis of medium-sized rings and macrocycles.

  2024cites this paper
• Organocatalyzed enantio- and diastereoselective isomerization of prochiral 1,3-cyclohexanediones into nonalactones bearing distant stereocenters

  2023cites this paper
• Divergent Cascade Ring Expansion Reactions of Acryloyl Imides.

  2023cites this paper
• Ring expansion reactions of PO-containing molecules.

  2023cites this paper
• Ring Expansion Strategies for the Synthesis of Medium Sized Ring and Macrocyclic Sulfonamides.

  2023cites this paper
• Synthesis of medium-ring lactams and macrocyclic peptide mimetics via conjugate addition/ring expansion cascade reactions

  2022cites this paper
• Macrolactonization Reactions Driven by a Pentafluorobenzoyl Group.

  2021cites this paper
• Ru-catalysed C(sp2)-H vinylation/annulation of benzoic acids and alkynes: rapid access to medium-sized lactones.

  2021cites this paper
• Synthesis of macrocyclic and medium-sized ring thiolactones via the ring expansion of lactams.

  2021cites this paper
• Nine-Membered Rings

  2021cites this paper
• Synthesis of in situ immobilized iron oxide nanoparticles (Fe 3 O 4 ) on microcrystalline cellulose: Ecofriendly and recyclable catalyst for Michael addition

  2021cites this paper
• Evaluating the Viability of Successive Ring‐Expansions Based on Amino Acid and Hydroxyacid Side‐Chain Insertion

  2020cites this paper
• Synthesis of 2,3-disubstituted indoles via a tandem reaction

  2020cites this paper
• One-pot reactions of three-membered rings giving N,O,S-heterocycles

  2020cites this paper
• Synthesis of naphtho[1′,2′:4,5]imidazo[1,2-a]pyridines via Rh(iii)-catalyzed C–H functionalization of 2-arylimidazo[1,2-a]pyridines with cyclic 2-diazo-1,3-diketones featuring with a ring opening and reannulation

  2020cites this paper
• A happy medium: the synthesis of medicinally important medium-sized rings via ring expansion

  2020cites this paper
• Synthesis of Spiro[5.n (n=6–8)]heterocycles through Successive Ring‐Expansion/Indole C‐2 Functionalization

  2020cites this paper
• Internal nucleophilic catalyst mediated cyclisation/ring expansion cascades for the synthesis of medium-sized lactones and lactams.

  2019cites this paper
• Nucleophilic-Addition-Initiated Ring Expansion and Selectivity in Anionic Fragmentation.

  2018cites this paper
• Synthesis of Benzannulated Medium-ring Lactams via a Tandem Oxidative Dearomatization-Ring Expansion Reaction.

  2018cites this paper
• Iterative Assembly of Macrocyclic Lactones using Successive Ring Expansion Reactions

  2018cites this paper