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Asymmetric, stereocontrolled total synthesis of (-)-brevianamide B

https://doi.org/10.1021/ja00158a048
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The α‐Hydroxy Ketone (α‐Ketol) and Related Rearrangements†
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Maremycins C and D, New Diketopiperazines, and Maremycins E and F, Novel Polycyclicspiro-Indole Metabolites Isolated fromStreptomycessp.
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Studies on the Biosynthesis of Paraherquamide: Synthesis and Incorporation of a Hexacyclic Indole Derivative as an Advanced Metabolite
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Studies on the Biosynthesis of Paraherquamide: Synthesis and Incorporation of a Hexacyclic Indole Derivative as an Advanced Metabolite
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Protection for the Carboxyl Group
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Protection for the Amino Group
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Amino Acids, Peptides, and Proteins
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Formation of Nitriles, Carboxylic Acids, and Derivatives by Alkylation, Acylation, and Substitution
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Protection for the Carboxyl Group
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Protection for the Amino Group
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Protecting‐Group‐Free Synthesis of Natural Products and Analogs, Part III
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Biomimetic Synthesis of Alkaloids with a Modified Indole Nucleus
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N‐Heterocyclic Carbene‐Catalyzed Umpolung Formal [3+3] Cycloaddition of Enals with Isatogens: Access to Fused Indolin‐3‐ones with a Tetrasubstituted Carbon Stereocenter
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Organocatalytic Asymmetric Transformations Involving the Cyclic Imine Moiety in Indole and Isoindole Related Heterocycles
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Recent Developments in Photo‐Catalyzed/Promoted Synthesis of Indoles and Their Functionalization: Reactions and Mechanisms
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PPh3‐Mediated Wittig‐Like/Mannich Tandem Reactions of 2‐Alkynylnitrobenzenes with Ketones for the Synthesis of 2,2‐Disubstituted Indolin‐3‐Ones
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Short, Enantioselective Total Synthesis of Stephacidin A
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Total Synthesis of Avrainvillamide (CJ‐17,665) and Stephacidin B
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A Concise Total Synthesis of the Notoamides C and D
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A Concise, Biomimetic Total Synthesis of Stephacidin A and Notoamide B
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Rapid Construction of the Cortistatin Pentacyclic Core
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Dual Catalysis for the Redox Annulation of Nitroalkynes with Indoles: Enantioselective Construction of Indolin‐3‐ones Bearing Quaternary Stereocenters
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Total Synthesis of Notoamides F, I, and R and Sclerotiamide
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Total Synthesis of (±)‐Baphicacanthcusine A Enabled by Sequential Ring Contractions
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Short, Enantioselective Total Synthesis of Stephacidin A
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Total Synthesis of Avrainvillamide (CJ‐17,665) and Stephacidin B
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A Concise Total Synthesis of the Notoamides C and D
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A Concise, Biomimetic Total Synthesis of Stephacidin A and Notoamide B
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Rapid Construction of the Cortistatin Pentacyclic Core
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Dual Catalysis for the Redox Annulation of Nitroalkynes with Indoles: Enantioselective Construction of Indolin‐3‐ones Bearing Quaternary Stereocenters
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Total Synthesis of Notoamides F, I, and R and Sclerotiamide
inferred← citeshttps://doi.org/10.1002/anie.202409139openalex-snapshot
Total Synthesis of (±)‐Baphicacanthcusine A Enabled by Sequential Ring Contractions
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Hydrogen‐Bonding Network Promoted [3+2] Cycloaddition: Asymmetric Catalytic Construction of Spiro‐pseudoindoxyl Derivatives
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Organocatalytic Asymmetric Cascade Aerobic Oxidation and Semipinacol Rearrangement Reaction: A Visible Light‐Induced Approach to Access Chiral 2,2‐Disubstituted Indolin‐3‐ones
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InCl3‐Mediated Addition of Indole to Isatogens: An Expeditious Synthesis of 13‐deoxy‐Isatisine A
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Organocatalytic Enantioselective Aza‐Friedel–Crafts Reaction of Cyclic Ketimines with Pyrroles using Imidazolinephosphoric Acid Catalysts
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Access to 3‐Oxindoles from Allylic Alcohols and Indoles
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Copper‐Catalyzed Tunable Oxygenative Rearrangement of Tetrahydrocarbazoles
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ChemInform Abstract: Asymmetric, Stereocontrolled Total Synthesis of (‐)‐Brevianamide B.
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Phosphoric Acid Catalyzed 1,2‐Rearrangements of 3‐Hydroxyindolenines to Indoxyls and 2‐Oxindoles: Reagent‐Controlled Regioselectivity Enabled by Dual Activation
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Synthesis of Aristotelia‐Type Alkaloids. Part XII. Total synthesis of (−)‐tasmanine. Stereoelectronic factors that control the rearrangement of 3H‐indol‐3‐ol derivatives to oxindoles ( = 1,3‐dihydro‐2H‐indol‐2‐ones) or to pseudoindoxyls ( =1,2‐dihydro‐3H‐indol‐3‐ones)
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Studies on the Biosynthesis of the Stephacidin and Notoamide Natural Products: A Stereochemical and Genetic Conundrum
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Efficient Domino Approach to Polysubstituted 2‐Hydroxyindole‐3,4‐(2H,5H)‐diones
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Formation and structure elucidation of two novel spiro[2H‐indol]‐3(1H)‐ones
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Solid-phase synthesis via 5-oxazolidinones. Ring opening reactions with amines and reaction monitoring by single bead FT-IR microspectroscopy
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Biosynthesis of Prenylated Alkaloids Derived from Tryptophan
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An efficient synthesis of 1′,4′-dihydro-2′H-spiro[azetidin-2,3′-quinolin]-2′-one
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Reinvestigation of dimerization of Z-N-alkylarylmethylideneindoxyls upon exposure to UV-vis radiation
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Design, synthesis and characterization of functionalized pyrazole derivatives bearing amide and sulfonamide moieties from aza-aurones
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Rearrangement of α-hydroxy imines to α-amino ketones: Mechanistic aspects and synthetic applications
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Synthèse d'analogues structuraux de thaxtomines, phytotoxines responsables de la gale de la pomme de terre
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Studies on the total synthesis of paraherquamide A. Stereocontrolled, asymmetric synthesis of α-alkyl-β-hydroxyproline derivatives
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Brevianamide A and B
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Pyrroles and their Benzo Derivatives: Reactivity
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Volume 2 References
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An improved synthesis of α,β-unsaturated nitrones relevant to the stephacidins and analogs thereof
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Development of chiral fluorinated alkyl derivatives of emixustat as drug candidates for the treatment of retinal degenerative diseases
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The synthetic versatility of alkoxycarbonyl- and hydroxymethyl-piperazine-2,5-diones
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A concise synthesis of d,l-brevianamide B via a biomimetically-inspired IMDA construction
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Concise, biomimetic total synthesis of d,l-marcfortine C
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Studies towards complex bridged alkaloids: regio- and stereocontrolled enolate chemistry of 2,5-diketopiperazines
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Synthetic studies toward paraherquamides E and F and related 13C-labeled putative biosynthetic intermediates: stereocontrolled synthesis of the α-alkyl-β-methylproline ring system
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Studies on paraherquamide biosynthesis: synthesis of deuterium-labeled 7-hydroxy-pre-paraherquamide, a putative precursor of paraherquamides A, E, and F
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Preparation of 2,2-disubstituted 1,2-dihydro-3H-indol-3-ones via oxidation of 2-substituted indoles and Mannich-type reaction
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A cationic cyclisation route to prenylated indole alkaloids: synthesis of malbrancheamide B and brevianamide B, and progress towards stephacidin A
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Synthesis and evaluation of C8-substituted 4.5-spiro lactams as Glycogen Phosphorylase a inhibitors
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Concise synthesis of the core bicyclo[2.2.2]diazaoctane ring common to asperparaline, paraherquamide, and stephacidin alkaloids
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Synthesis towards complex bridged alkaloids derived from diketopiperazines: a cationic cascade approach to stephacidins, paraherquamides and related systems
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Coupling of activated esters to gramines in the presence of ethyl propiolate under mild conditions
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Photocatalytic aerobic oxidation/semipinacol rearrangement sequence: a concise route to the core of pseudoindoxyl alkaloids
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Speramides A–B, two new prenylated indole alkaloids from the freshwater-derived fungus Aspergillus ochraceus KM007
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Acid-mediated aryl migration reaction of C-3 aryl substituted pyrrolidinoindolines
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Recent advances in the construction of isoindolo[2,1-a]indol/indolin-6-ones via C C cross-coupling reactions
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B(C6F5)3-catalyzed regio- and stereoselective cyanation of isatogens and their derivatives
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Reactions of substituted 2,3-dihydro-1 H -indol-3-ones and pyrrolo[2,3- b ]pyridin-3-ones with Wittig and Horner–Emmons reagents: synthesis of 7-azatryptamine
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Biosynthesis of brevianamides A and B: in search of the biosynthetic diels-alder construction
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Regio- and diastereoselective dialkylation of (4S)-2,4-dimethyl-2,4-dihydro-1H-pirazino[2,1-b]quinazoline-3,6-dione
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A total synthesis of spirocyclic alkaloids via an intramolecular SN2′ lactam enolate alkylation
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Piperazine-2,5-diones and Related Lactim Ethers
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Chapter 12 Prenylphenols
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Asymmetrically induced alkylation of 2-benzyl-4-isopropyl-2,4-dihydro-1H-pyrazino[2,1-b]quinazoline-3,6-dione
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Enantioselective synthesis of unsaturated amino acids using p-methoxybenzylamine as an ammonia equivalent
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Antineoplastic agents 323. Isolation and structure of phakellistatin 6 from a Chuuk archipelago marine sponge
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Antineoplastic Agents 390. Isolation and Structure of Phakellistatin 12 from a Chuuk Archipelago Marine Sponge
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Synthesis and Modification of Marcfortine and Paraherquamide Class of Anthelmintics
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The Mutually Inspiring Biological and Chemical Synthesis of Fungal Bicyclo[2.2.2]diazaoctane Indole Alkaloids
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Dieckmann Condensation of Ugi N-Acylamino Amide Product: Facile Access to Functionalized 2,2-Disubstituted Indolin-3-ones
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Pd-Catalyzed Asymmetric Allylation Reaction of 2-Aryl-3H-indol-3-ones with Allyltrimethylsilane
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Enantioselective Synthesis of C2-Quaternary Indolin-3-ones by Pt-Catalyzed Alkynylation of 2-Aryl-3 H -indol-3-one with Alkynylsilanes
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Intermolecular Diels–Alder Cycloaddition for the Construction of Bicyclo[2.2.2]diazaoctane Structures: Formal Synthesis of Brevianamide B and Premalbrancheamide
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The Cs2CO3–Catalyzed Reaction of 2-Oxindoles with Enones for the Preparation of Indolin-3-Ones and Their Further Transformation
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Further Investigation of the Intermolecular Diels–Alder Cycloaddition for the Synthesis of Bicyclo[2.2.2]diazaoctane Alkaloids
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Gold-Catalyzed Cascade Reactions of 4H-Furo[3,2-b]indoles with Allenamides: Synthesis of Indolin-3-one Derivatives
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Copper(0)/PPh3-Mediated Bisheteroannulations of o-Nitroalkynes with Methylketoximes Accessing Pyrazo-Fused Pseudoindoxyls
inferred← citeshttps://doi.org/10.1021/acs.orglett.2c02971openalex-snapshot
Expedited Total Synthesis of (±)-Brevianamide A via the Strategic Use of Gold(I) Catalysis
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Ru-Catalyzed Redox-Neutral Cleavage of the N–O Bond in Isoxazolidines: Isatogens to Pseudoindoxyls via a One-Pot [3 + 2]-Cycloaddition/N–O Cleavage
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Gold/Copper-Co-catalyzed Tandem Reactions of 2-Alkynylanilines: A Synthetic Strategy for the C2-Quaternary Indolin-3-ones
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Catalytic Asymmetric Mukaiyama–Mannich Reaction of Cyclic C-Acylimines with Difluoroenoxysilanes: Access to Difluoroalkylated Indolin-3-ones
inferred← citeshttps://doi.org/10.1021/acs.orglett.9b01965openalex-snapshot
Organocatalytic Asymmetric Dearomative Oxyalkylation of Indoles Enables Access to C2-Quaternary Indolin-3-ones
inferred← citeshttps://doi.org/10.1021/acscatal.4c00793openalex-snapshot
N-Heterocyclic Carbene-Catalyzed Imine Umpolung/Semipinacol Rearrangement Cascade for the Synthesis of Indoxyls
inferred← citeshttps://doi.org/10.1021/cr200055gopenalex-snapshot
Semipinacol Rearrangement in Natural Product Synthesis
inferred← citeshttps://doi.org/10.1021/ja037687iopenalex-snapshot
Studies on the Biosynthesis of Asperparaline A: Origin of the Spirosuccinimde Ring System
inferred← citeshttps://doi.org/10.1021/ja0510616openalex-snapshot
Enantioselective Synthesis of Stephacidin B
inferred← citeshttps://doi.org/10.1021/ja202706gopenalex-snapshot
Chemoselective and Enantioselective Oxidation of Indoles Employing Aspartyl Peptide Catalysts
inferred← citeshttps://doi.org/10.1021/ja204597kopenalex-snapshot
Concise Total Synthesis and Stereochemical Revision of all (−)-Trigonoliimines
inferred← citeshttps://doi.org/10.1021/ja2075086openalex-snapshot
[4 + 2] Cyclocondensation Reactions of Tungsten–Dihydropyridine Complexes and the Generation of Tri- and Tetrasubstituted Piperidines
inferred← citeshttps://doi.org/10.1021/ja2093212openalex-snapshot
Biochemical Characterization of NotB as an FAD-Dependent Oxidase in the Biosynthesis of Notoamide Indole Alkaloids
inferred← citeshttps://doi.org/10.1021/ja952666copenalex-snapshot
Stereocontrolled Total Synthesis of (+)-Paraherquamide B
inferred← citeshttps://doi.org/10.1021/ja9814366openalex-snapshot
The Role of Monomer in Alkylation Reactions of the Lithium Enolate of p -Phenylisobutyrophenone in Tetrahydrofuran 1
inferred← citeshttps://doi.org/10.1021/jo0100897openalex-snapshot
Intermolecular and Intramolecular Diels−Alder Cycloadditions of 3-Ylidenepiperazine-2,5-diones and 5-Acyloxy-2(1H)-pyrazinones
inferred← citeshttps://doi.org/10.1021/jo1006812openalex-snapshot
Aiming for the Ideal Synthesis
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Natural Products Synthesis: Enabling Tools To Penetrate Nature’s Secrets of Biogenesis and Biomechanism
inferred← citeshttps://doi.org/10.1021/jo201955copenalex-snapshot
N-Alkenyl Indoles as Useful Intermediates for Alkaloid Synthesis
inferred← citeshttps://doi.org/10.1021/jo4020358openalex-snapshot
Total Synthesis, Stereochemical Assignment, and Biological Activity of All Known (−)-Trigonoliimines
inferred← citeshttps://doi.org/10.1021/jo5022647openalex-snapshot
Chiroptical Studies on Brevianamide B: Vibrational and Electronic Circular Dichroism Confronted
inferred← citeshttps://doi.org/10.1021/ol5024163openalex-snapshot
Total Synthesis of Aspeverin via an Iodine(III)-Mediated Oxidative Cyclization
inferred← citeshttps://doi.org/10.1021/ol701845topenalex-snapshot
Improved Biomimetic Total Synthesis of d , l -Stephacidin A
inferred← citeshttps://doi.org/10.1023/b:phac.0000048140.06266.63openalex-snapshot
Chemistry of N-(1H-indol-3-ylmethyl)-N,N-dimethylamine (Gramine): A Review
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Total synthesis of brevianamide A
inferred← citeshttps://doi.org/10.1039/a802702aopenalex-snapshot
The biosynthetic origin of diketopiperazines derived from D-proline
inferred← citeshttps://doi.org/10.1039/b207530jopenalex-snapshot
Reactions of 2-[(2-arylimino-2-cyano-1,1-dimethylethyl)arylamino]-3-methylbut-2-enenitrile with copper(ii) acetate: synthesis of 2-(2,3-dihydro-2,2-dimethyl-3-oxo-1H-indol-1-yl)-3-methylbut-2-enenitriles
inferred← citeshttps://doi.org/10.1039/c1cc16510kopenalex-snapshot
Rapid access to polycyclic indolines related to the stephacidin alkaloids using a radical cascade
inferred← citeshttps://doi.org/10.1039/c2ob25316jopenalex-snapshot
Mechanism of the N-protecting group dependent annulations of 3-aryloxy alkynyl indoles under gold catalysis: a computational study
inferred← citeshttps://doi.org/10.1039/c3sc52803kopenalex-snapshot
Catalytic enantioselective synthesis of 2-(2-hydroxyethyl)indole scaffolds via consecutive intramolecular amido-cupration of allenes and asymmetric addition of carbonyl compounds
inferred← citeshttps://doi.org/10.1039/c6ra14904aopenalex-snapshot
Penicimutamides A–C: rare carbamate-containing alkaloids from a mutant of the marine-derived Penicillium purpurogenum G59
inferred← citeshttps://doi.org/10.1039/c7np00042aopenalex-snapshot
Structural and stereochemical diversity in prenylated indole alkaloids containing the bicyclo[2.2.2]diazaoctane ring system from marine and terrestrial fungi
inferred← citeshttps://doi.org/10.1039/c7ra02446kopenalex-snapshot
Penicimutamides D–E: two new prenylated indole alkaloids from a mutant of the marine-derived Penicillium purpurogenum G59
inferred← citeshttps://doi.org/10.1039/c9cc02956gopenalex-snapshot
Direct oxidative dearomatization of indoles: access to structurally diverse 2,2-disubstituted indolin-3-ones
inferred← citeshttps://doi.org/10.1039/c9ra02569copenalex-snapshot
Synthesis of tetracyclic indolin-3-ones through Pd-catalyzed intramolecular deacetylative dearomatization of 3-acetoxy-indoles
inferred← citeshttps://doi.org/10.1039/d0cc06418aopenalex-snapshot
Catalytic asymmetric formal [3+2] cycloaddition of isatogens with azlactones to construct indolin-3-one derivatives
inferred← citeshttps://doi.org/10.1039/d1sc03533aopenalex-snapshot
A general approach to 2,2-disubstituted indoxyls: total synthesis of brevianamide A and trigonoliimine C
inferred← citeshttps://doi.org/10.1039/d1sc05801kopenalex-snapshot
Unified total synthesis of the brevianamide alkaloids enabled by chemical investigations into their biosynthesis
inferred← citeshttps://doi.org/10.1039/d3ra03641copenalex-snapshot
An efficient method to access spiro pseudoindoxyl ketones: evaluation of indoxyl and their N -benzylated derivatives for inhibition of the activity of monoamine oxidases
inferred← citeshttps://doi.org/10.1039/d4ob00915kopenalex-snapshot
A comprehensive understanding of the mechanism of the biomimetic total synthesis of brevianamide A
inferred← citeshttps://doi.org/10.1039/d6nj01151aopenalex-snapshot
PPh 3 -Mediated synthesis of multifunctional indolin-3-one derivatives from 2-(ethynyl)nitrobenzenes and aryl ketones
inferred← citeshttps://doi.org/10.1039/np9860300353openalex-snapshot
Recent progress in the chemistry of indole alkaloids and mould metabolites
inferred← citeshttps://doi.org/10.1039/p19910002495openalex-snapshot
Synthesis of (4S,5R)-(–)-4-methyl-5-phenyloxazolidine-2-selone: a chiral auxiliary reagent capable of detecting the enantiomers of (R,S)-lipoic acid by 77 Se nuclear magnetic resonance spectroscopy
inferred← citeshttps://doi.org/10.1039/p19910003149openalex-snapshot
Asymmetric construction of α,α–disubstituted cyclobutanones–enantioselective total synthesis of (–)-frontalin
inferred← citeshttps://doi.org/10.1080/10715762.2016.1223295openalex-snapshot
Oxidative radical cyclizations of diketopiperazines bearing an amidomalonate unit. Heterointermediate reaction sequences toward the asperparalines and stephacidins
inferred← citeshttps://doi.org/10.1248/cpb.50.711openalex-snapshot
Total Synthesis and Biosynthesis of the Paraherquamides: An Intriguing Story of the Biological Diels–Alder Construction
inferred← citeshttps://doi.org/10.1515/9783110867855.42openalex-snapshot
3 Techniques used in the analysis of optically active compounds. 3.2 Nuclear magnetic resonance
inferred← citeshttps://doi.org/10.3389/fchem.2022.938626openalex-snapshot
The Secondary Metabolites and Biosynthetic Diversity From Aspergillus ochraceus
inferred← citeshttps://doi.org/10.3390/books978-3-03842-132-0openalex-snapshot
Marine Compounds and Cancer
inferred← citeshttps://doi.org/10.3390/books978-3-03842-766-7openalex-snapshot
Marine Compounds and Cancer 2017
inferred← citeshttps://doi.org/10.3390/md15020043openalex-snapshot
Brevianamides and Mycophenolic Acid Derivatives from the Deep-Sea-Derived Fungus Penicillium brevicompactum DFFSCS025
inferred← citeshttps://doi.org/10.3390/molecules25020419openalex-snapshot
Oxidative Dearomative Cross-Dehydrogenative Coupling of Indoles with Diverse C-H Nucleophiles: Efficient Approach to 2,2-Disubstituted Indolin-3-ones
inferred← citeshttps://doi.org/10.3987/com-06-s(k)39openalex-snapshot
Versatile Synthesis of 2,2-Disubstituted Indolinones via Protected Indolones Generated by One-Pot Multi-oxidation of 2-Substituted Indoles
inferred← citeshttps://doi.org/10.3987/com-13-12669openalex-snapshot
Dimethyldioxirane Oxidation of N-Substituted-2-methylindoles to Indoxyls and Bisindoxyls
inferred← citeshttps://doi.org/10.3998/ark.5550190.p008.840openalex-snapshot
Ceric ammonium nitrate oxidation of N-(p-methoxybenzyl)lactams: competing formation of N-(hydroxymethyl)δ-lactams
inferred← citeshttps://doi.org/10.5059/yukigoseikyokaishi.73.821openalex-snapshot
Synthetic Development of 2,2-Disubstituted Indolin-3-ones Using Mannich-type Reactions and Its Application to Natural Product Synthesis
inferred← citeshttps://doi.org/10.6023/cjoc202506013openalex-snapshot
PPh 3 -Mediated One-Pot Synthesis of Indolin-3-ones from 2-Alkynylnitrobenzenes and Indoles
inferred← citeshttps://doi.org/10.7164/antibiotics.44.492openalex-snapshot
New paraherquamide antibiotics with anthelmintic activity.
inferred← citeshttps://doi.org/10.7164/antibiotics.46.1355openalex-snapshot
Further novel metabolites of the paraherquamide family.
inferred← citeshttps://doi.org/10.7164/antibiotics.50.840openalex-snapshot
Novel Anthelmintic Metabolites from an Aspergillus Species; the Aspergillimides.
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