Chemistry and biology of diazonamide A: second total synthesis and biological investigations.

As an especially unique target for chemical synthesis, diazonamide A has the potential to be constructed through a plethora of synthetic routes, each attended by different challenges and opportunities for discovery. In this article, we detail our second total synthesis of diazonamide A through a sequence entirely distinct from that employed in our first campaign, one whose success required the development of several special strategies and tactics. We also disclose our complete studies regarding the chemical biology of diazonamide A and its structural congeners, and more fully delineate the scope of our protocol for Robinson-Gabriel cyclodehydration using pyridine-buffered POCl(3).

• Publication year

  2004

• Venue

  Journal of the American Chemical Society

• Publication date

  2004-09-18

• Fields of study

  Biology, Medicine, Chemistry

• Identifiers
  DOI 10.1021/JA040093APMID 15469287
• 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.

• Studies toward diazonamide A: development of a hetero-pinacol macrocyclization cascade for the construction of the bis-macrocyclic framework of the originally proposed structure.

  2004cited by this paper
• A synthesis of the diazonamide heteroaromatic biaryl macrocycle/hemiaminal core.

  2004cited by this paper
• Studies toward diazonamide A: initial synthetic forays directed toward the originally proposed structure.

  2004cited by this paper
• A new method for the stereoselective synthesis of alpha- and beta-glycosylamines using the Burgess reagent.

  2004cited by this paper
• Diazonamide A and a synthetic structural analog: disruptive effects on mitosis and cellular microtubules and analysis of their interactions with tubulin.

  2003cited by this paper
• Exceptional redox and photophysical properties of a triply fused diporphyrin-C60 conjugate: novel scaffolds for multicharge storage in molecular scale electronics.

  2003cited by this paper
• A new method for the synthesis of nonsymmetrical sulfamides using burgess-type reagents.

  2003cited by this paper
• A concise and flexible total synthesis of (-)-diazonamide A.

  2003cited by this paper
• The second total synthesis of diazonamide A.

  2003cited by this paper
• Total synthesis of diazonamide A.

  2002cited by this paper
• A novel regio- and stereoselective synthesis of sulfamidates from 1,2-diols using Burgess and related reagents: a facile entry into beta-amino alcohols.

  2002cited by this paper
• Diazonamide synthesis studies: use of Negishi coupling to fashion diazonamide-related biaryls with defined axial chirality.

  2002cited by this paper
• 3-(Diethoxyphosphoryloxy)-1,2,3-benzotriazin-4(3H)-one (DEPBT): a new coupling reagent with remarkable resistance to racemization.

  1999cited by this paper
• Total Syntheses of Vancomycin and Eremomycin Aglycons.

  1998cited by this paper

• Photoinduced arylation of 3-acyl-substituted indoles with diaryliodonium triflates enabled by electron donor − acceptor complexes

  2025cites this paper
• Natural and synthetic 5‐(3′‐indolyl)oxazoles: Biological activity, chemical synthesis and advanced molecules

  2024cites this paper
• Development of Potent Microtubule Targeting Agent by Structural Simplification of Natural Diazonamide.

  2024cites this paper
• Non-stoichiometric problem of photocatalytic water splitting on γ-GaO: Cause and solution

  2024cites this paper
• Support Studies Toward the Alkaloids Mescengricin and Lysiformine focused on Oxazole-Olefin Cycloadditions

  2024cites this paper
• Domino Michael/Oxa-Michael Reactions of the Unsymmetric Double Michael Acceptor for Access to Bicyclic Furo[2,3-b]pyrrole.

  2024cites this paper
• Pd-Catalyzed C(2)—H Arylation of 3-(2-Aminopyrimidin-4-yl)indoles

  2023cites this paper
• Organocatalytic intramolecular (4 + 2) annulation of enals with ynamides: atroposelective synthesis of axially chiral 7-aryl indolines

  2023cites this paper
• Enzymatic Benzofuranoindoline Formation in the Biosynthesis of the Strained Bridgehead Bicyclic Dipeptide (+)-Azonazine A.

  2023cites this paper
• Synthesis and Reactivity of Fluorinated Dithiocarboxylates to Prepare Thioamides—Effective Access to a 4-Styrenylthioamide-Cinchona Alkaloid Monomer

  2023cites this paper
• Chemical synthesis in competition with global genome mining and heterologous expression for the preparation of dimeric indole-derived 2,5-dioxopiperazines.

  2022cites this paper
• Visible-Light 2,4-Dinitrophenol-Mediated Photoannulation of α-Azidochalcones into 2,5-Diaryloxazoles.

  2022cites this paper
• Heck macrocyclization in natural product total synthesis.

  2021cites this paper
• Total Synthesis of Homo- and Heterodimeric Bispyrrolidinoindoline Dioxopiperazine Natural Products.

  2021cites this paper
• One‐pot Suzuki Coupling‐Knoevenagel Condensation Tandem Reaction Catalyzed by a Recyclable Magnetic Bifunctional Catalyst

  2021cites this paper
• Natural products originated from the oxidative coupling of tyrosine and tryptophan: biosynthesis and bioinspired synthesis.

  2020cites this paper
• Synthesis of 2,5-diaryloxazoles through rhodium-catalyzed annulation of triazoles and aldehydes

  2020cites this paper
• The quest for supernatural products: the impact of total synthesis in complex natural products medicinal chemistry.

  2020cites this paper
• Synthesis of α-Amidoketones through the Cascade Reaction of Carboxylic Acids with Vinyl Azides under Catalyst-Free Conditions.

  2020cites this paper
• α‐Amidoaldehydes as Substrates in Rhodium‐Catalyzed Intermolecular Alkyne Hydroacylation: The Synthesis of α‐Amidoketones

  2020cites this paper
• Unconventional Macrocyclizations in Natural Product Synthesis

  2020cites this paper
• Total Synthesis of Bacterial 5-(3-Indolyl)oxazole Alkaloids: Pimprinols A–C

  2019cites this paper
• A Mild Synthesis of Bicyclic Alkoxyoxazolium Salts from Proline and Pipecolic Acid Derivatives

  2019cites this paper
• 14β-(Isoxazol-3-yl)methylestrane Steroids: Chemoselective Synthesis and Transformations with Heterocyclic Ring Opening

  2019cites this paper
• Homo- and Heterobimetallic Complexes Bearing NHC Ligands: Applications in α-Arylation of Amide, Suzuki-Miyaura Coupling Reactions, and Tandem Catalysis

  2019cites this paper
• Ruthenium(ii)-catalyzed C–O/C–S cyclization for the synthesis of 5-membered O-containing and S-containing heterocycles

  2019cites this paper
• Stereoconfining macrocyclizations in the total synthesis of natural products.

  2019cites this paper
• Catalytic Asymmetric Dearomative [3+2] Cyclisation of 1,4‐Quinone with 2,3‐Disubstituted Indoles

  2019cites this paper
• Metal-free iodine(iii)-promoted synthesis of 2,5-diaryloxazoles.

  2018cites this paper
• A consecutive one-pot two-step approach to trifluoromethylated pyrazolo[4ʹ,3ʹ:5,6]pyrano[2,3-b]indoles promoted by molecular iodine

  2018cites this paper
• Catalytic Enantioselective 1,3-Alkyl Shift in Alkyl Aryl Ethers: Efficient Synthesis of Optically Active 3,3'-Diaryloxindoles.

  2018cites this paper
• Recent Applications of Kagan's Reagent (SmI2) in Natural Product Synthesis

  2018cites this paper
• Regiocontrolled Direct C-H Arylation of Indoles at the C4 and C5 Positions.

  2017cites this paper
• Exploring the Boundaries of "Practical": De Novo Syntheses of Complex Natural Product-Based Drug Candidates.

  2017cites this paper
• A Zwitterionic Palladium(II) Complex as a Precatalyst for Neat‐Water‐Mediated Cross‐Coupling Reactions of Heteroaryl, Benzyl, and Aryl Acid Chlorides with Organoboron Reagents

  2017cites this paper
• Regioselective Friedel–Crafts Reaction of Electron-Rich Benzenoid Arenes and Spiroepoxyoxindole at the Spiro-Centre: Efficient Synthesis of Benzofuroindolines and 2H- Spiro[benzofuran]-3,3′-oxindoles

  2016cites this paper
• Catalytic asymmetric synthesis of axially chiral 2-amino-1,1′-biaryl compounds by phase-transfer-catalyzed kinetic resolution and desymmetrization

  2016cites this paper
• Synthesis of 2-oxindoles via 'transition-metal-free' intramolecular dehydrogenative coupling (IDC) of sp2 C–H and sp3 C–H bonds

  2016cites this paper
• Recent Advances in the Synthesis of 1,3-Azoles.

  2016cites this paper
• Chiral Bidentate NHC Ligands Based on the 1,1'-Binaphthyl Scaffold: Synthesis and Application in Transition-Metal-Catalyzed Asymmetric Reactions.

  2016cites this paper
• The First Enantioselective Organocatalytic Synthesis of 3-Spiro-α-Alkylidene-γ-Butyrolactone Oxindoles.

  2016cites this paper
• Synthesis of Substituted Oxazoles by Visible-Light Photocatalysis.

  2016cites this paper
• Catalytic transformation of esters of 1,2-azido alcohols into α-amido ketones.

  2016cites this paper
• Formal Total Synthesis of Diazonamide A by Indole Oxidative Rearrangement.

  2016cites this paper
• Thiazole: A Review on Chemistry, Synthesis and Therapeutic Importance of its Derivatives.

  2016cites this paper
• The preparation of annulated 1,3-oxazoles from 1,3,2-oxazaphospholes and aldehydes

  2016cites this paper
• One-pot synthesis of spirofluorenyl- and spiroindeno[1,2-b]indolyl oxindoles via sequential inter- and intramolecular Friedel–Crafts reactions

  2016cites this paper
• Stereoselective synthesis of the diazonamide a macrocyclic core.

  2015cites this paper
• Biomimetic semi-synthesis of fradcarbazole A and its analogues

  2015cites this paper
• Enantiocontrolled synthesis of a tetracyclic aminal corresponding to the core subunit of diazonamide A.

  2015cites this paper
• A convenient synthesis of 3-formyl-2-thioacetamide-indole derivatives via the one-pot reaction of indolin-2-thiones, isocyanides and chloroacetylchloride

  2015cites this paper
• Electrolytic macrocyclizations: scalable synthesis of a diazonamide-based drug development candidate.

  2015cites this paper
• Crystal structure of 4-tert-butyl-2-{2-[N-(3,3-dimethyl-2-oxobutyl)-N-isopropylcarbamoyl]phenyl}-1-isopropyl-1H-imidazol-3-ium perchlorate

  2015cites this paper
• A General and Practical Palladium-Catalyzed Direct α-Arylation of Amides with Aryl Halides.

  2014cites this paper
• Friedel-Crafts alkylations of electron-rich aromatics with 3-hydroxy-2-oxindoles: scope and limitations.

  2014cites this paper
• Bioinspired direct access to benzofuroindolines by oxidative [3 + 2] annulation of phenols and indoles.

  2014cites this paper
• Regioselective hydroarylation reactions of C3 electrophilic N-acetylindoles activated by FeCl3: an entry to 3-(hetero)arylindolines.

  2014cites this paper
• Synthesis and MRSA PK inhibitory activity of thiazole containing deoxytopsentin analogues

  2014cites this paper
• 2.09 The Aldol Reaction: Group IV Enolates (Mukaiyama, Enol Ethers)

  2014cites this paper
• Ascidians (Tunicates)–2

  2014cites this paper
• General Suzuki Coupling of Heteroaryl Bromides by Using Tri‐tert‐butylphosphine as a Supporting Ligand

  2014cites this paper
• Iodine‐Promoted Sequential C(sp3) ? H Functionalization Reactions: An Annulation Strategy for the Construction of 3‐Methylthio‐4‐arylmaleimides

  2014cites this paper
• Intramolecular Larock Indole Synthesis for the Preparation of Tricyclic Indoles and Its Application in the Synthesis of Tetrahydropyrroloquinoline and Fargesine.

  2014cites this paper
• Rh(I)-catalyzed asymmetric 1,2-additions of arylboronic acids to isatins with chiral sulfur–alkene hybrid ligands

  2014cites this paper
• Applications of Bartoli indole synthesis.

  2014cites this paper
• Intramolecular Larock indole synthesis: preparation of 3,4-fused tricyclic indoles and total synthesis of fargesine.

  2013cites this paper
• An efficient synthesis of novel chromeno[3’, 4’：5, 6]pyrano[2, 3-b]indole derivatives

  2013cites this paper
• Enantioselective photoredox catalysis enabled by proton-coupled electron transfer: development of an asymmetric aza-pinacol cyclization.

  2013cites this paper
• The Claisen rearrangement in the syntheses of bioactive natural products

  2013cites this paper
• Kinetic resolution of axially chiral 2-amino-1,1'-biaryls by phase-transfer-catalyzed N-allylation.

  2013cites this paper
• DDQ-induced dehydrogenation of heterocycles for C-C double bond formation: synthesis of 2-thiazoles and 2-oxazoles.

  2013cites this paper
• Absolute Stereochemical Assignment of SCH 71450, a Selective Dopamine D4 Receptor Antagonist, Through Enantioselective Epimer Synthesis

  2013cites this paper
• Dichloro[1,1′‐bis(diphenylphosphino)ferrocene]palladium(II)

  2013cites this paper
• Mukaiyama Aldol Reactions in Aqueous Media

  2013cites this paper
• Intramolecular dehydrogenative coupling of sp2 C-H and sp3 C-H bonds: an expeditious route to 2-oxindoles.

  2012cites this paper
• Synthesis of oxazoles through copper-mediated aerobic oxidative dehydrogenative annulation and oxygenation of aldehydes and amines.

  2012cites this paper
• Morita–Baylis–Hillman reactions of isatins with allenoates

  2012cites this paper
• Constructing molecular complexity and diversity: total synthesis of natural products of biological and medicinal importance.

  2012cites this paper
• Ynamides: stable ligand equivalents of unstable oxazol-4-ylidenes (novel mesoionic carbenes).

  2012cites this paper
• Lewis acid-catalyzed Friedel-Crafts alkylations of 3-hydroxy-2-oxindole: an efficient approach to the core structure of azonazine.

  2012cites this paper
• Room‐Temperature Suzuki–Miyaura Coupling of Heteroaryl Chlorides and Tosylates

  2012cites this paper
• The Chemistry of Marine Tunicates

  2012cites this paper
• A Novel One‐pot Synthesis of Biaryl Derivatives by Sequential Strategies via Suzuki Coupling/Knoevenagel Condensation in Aqueous Medium at Room Temperature

  2012cites this paper
• A Novel Method for One‐pot Synthesis of Furo[3,2‐c]coumarin Derivatives from 4‐Hydroxycoumarin and Arylglyoxal under Microwave Irradiation

  2012cites this paper
• Gold(I)-catalyzed synthesis of furans and pyrroles via alkyne hydration

  2011cites this paper
• Oxazole and its derivatives

  2011cites this paper
• Metal‐Catalyzed Borylation of CH and CHalogen Bonds of Alkanes, Alkenes, and Arenes for the Synthesis of Boronic Esters

  2011cites this paper
• Atroposelective total synthesis of axially chiral biaryl natural products.

  2011cites this paper
• [4+2] Cycloaddition on densely functionalized cyclopentadiene

  2011cites this paper
• Biomimetic Synthesis of Indole‐Oxidized and Complex Peptide Alkaloids

  2011cites this paper
• Five-Membered Ring Systems: With N and S (Se) Atoms

  2011cites this paper
• Intra- and intermolecular thermal transformations of 2-acyl- and 2-alkoxycarbonyl-N-phthalimidoaziridines

  2011cites this paper
• 2-Iodoxybenzoic acid--a simple oxidant with a dazzling array of potential applications.

  2011cites this paper
• 2‐Iodoxybenzoesäure – ein einfaches Oxidationsmittel mit einer Vielfalt an Anwendungsmöglichkeiten

  2011cites this paper
• Formal Total Synthesis of Diazonamide A

  2011cites this paper
• Development and Applications of an Oxazole-Forming Reaction

  2011cites this paper
• General synthesis of mono-, di-, and tri-acetylated indoles from indolin-2-ones

  2011cites this paper
• Total synthesis of diazonamide A.

  2011cites this paper
• El premio Nobel en Química 2010

  2011cites this paper
• An approach to the bis-oxazole macrocycle of diazonamides.

  2011cites this paper