Total syntheses of (±)-gephyrotoxin and (±)-perhydrogephyrotoxin
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- 資料種別
- 記事
- 著者・編者
- Kenji ShirokaneYuya TanakaMakoto Yoritate
- 出版年月日等
- 2015-01-20
- 出版年（W3CDTF）
- 2015-01-20
- タイトル（掲載誌）
- Bulletin of the Chemical Society of Japan
- 巻号年月日等（掲載誌）
- 88(4)
- 掲載巻
- 88(4)
- ISSN（掲載誌）
- 1348-0634
- ISSN-L（掲載誌）
- 0009-2673
- 本文の言語コード
- eng
- DOI
- 10.1246/bcsj.20140398
- 国立国会図書館永続的識別子
- info:ndljp/pid/11343187
- コレクション（共通）
- コレクション（障害者向け資料：レベル1）
- コレクション（個別）
- 国立国会図書館デジタルコレクション > 電子書籍・電子雑誌 > 学術機関 > 学協会
- 収集根拠
- オンライン資料収集制度
- 受理日（W3CDTF）
- 2019-08-27T20:45:33+09:00
- 保存日（W3CDTF）
- 2019-08-27
- 記録形式（IMT）
- application/pdf
- オンライン閲覧公開範囲
- 国立国会図書館内限定公開
- デジタル化資料送信
- 図書館・個人送信対象外
- 遠隔複写可否（NDL）
- 可
- 掲載誌（国立国会図書館永続的識別子）
- info:ndljp/pid/11343184
- 連携機関・データベース
- 国立国会図書館 : 国立国会図書館デジタルコレクション
- コレクション（個別）
- 国立国会図書館デジタルコレクション > 電子書籍・電子雑誌 > 学術機関 > 学協会
- オンライン閲覧公開範囲
- 国立国会図書館内限定公開
- デジタル化資料送信
- 図書館・個人送信対象外
- 遠隔複写可否（NDL）
- 可
- 所蔵機関
- 国立国会図書館
- 請求記号
- Z53-B35
- 関連情報（国立国会図書館永続的識別子）
- info:ndljp/pid/11343187
- 連携機関・データベース
- 国立国会図書館 : 国立国会図書館雑誌記事索引
- 書誌ID（NDLBibID）
- 026322139
- 整理区分コード
- 632
- 要約等
- This article describes the full details of our total syntheses of gephyrotoxin and perhydrogephyrotoxin. Our central strategy toward the total synthesis is based on the use of an <i>N</i>-methoxy group as a reactivity control element. The <i>N</i>-methoxyamide group enabled unique transformations, involving i) the direct coupling reaction of the <i>N</i>-methoxyamide with an aldehyde, and ii) the amide-selective reductive allylation. These reactions were never accomplished without the assistance of the <i>N</i>-methoxy group. The amide-selective reductive allylation of the <i>N</i>-methoxyamide was especially practical, and excluded a number of extra steps including protecting group manipulations and redox reactions in the total syntheses.
- DOI
- 10.1246/bcsj.20140398
- オンライン閲覧公開範囲
- インターネット公開
- 連携機関・データベース
- 科学技術振興機構 : J-STAGE
- 要約等
- This article describes the full details of our total syntheses of gephyrotoxin and perhydrogephyrotoxin. Our central strategy toward the total synthesis is based on the use of an <i>N</i>-methoxy group as a reactivity control element. The <i>N</i>-methoxyamide group enabled unique transformations, involving i) the direct coupling reaction of the <i>N</i>-methoxyamide with an aldehyde, and ii) the amide-selective reductive allylation. These reactions were never accomplished without the assistance of the <i>N</i>-methoxy group. The amide-selective reductive allylation of the <i>N</i>-methoxyamide was especially practical, and excluded a number of extra steps including protecting group manipulations and redox reactions in the total syntheses.
- DOI
- 10.1246/bcsj.2014039810.1002/chin.201537221
- オンライン閲覧公開範囲
- インターネット公開
- 関連情報（URI）
- 参照
- Asymmetric Total Synthesis of Fasicularin by Chiral <i>N</i>-Alkoxyamide StrategyEnantioselective Total Syntheses of (+)-Ganocin A and (−)-Cochlearol BIridium-Catalyzed Chemoselective Reductive Nucleophilic Addition to <i>N</i>-MethoxyamidesTotal synthesis of complex alkaloids by nucleophilic addition to amidesDevelopment of a Chiral N-Alkoxyamide Strategy and Application to the Asymmetric Total Synthesis of FasicularinReductive approach to nitrones from N-siloxyamides and N-hydroxyamides<i>N</i>-アルコキシアミド基への求核付加反応の開発とゲフィロトキシンの全合成Iridium-catalyzed reductive nucleophilic addition to tertiary amidesReductive functionalization of carboxamides : a recent update#
- 参照
- Concise Synthesis of α-Trisubstituted Amines from Ketones Using <i>N</i>-MethoxyaminesEine einfache Synthese von rac.-GephyranA novel synthetic route to (±)-perhydrogephyrotoxinProtecting-group-free synthesis as an opportunity for inventionThree-Component Coupling Reactions of Thioformamides with Organolithium and Grignard Reagents Leading to Formation of Tertiary Amines and a Thiolating AgentRecent development of peptide coupling reagents in organic synthesisNucleophilic addition to N-alkoxyamidesDirect Chemoselective Allylation of Inert Amide CarbonylsIndium Triiodide Catalyzed Reductive Functionalization of Amides via the Single-Stage Treatment of Hydrosilanes and Organosilicon NucleophilesOn the absolute configuration of gephyrotoxinA General Model for Selectivity in Olefin Cross MetathesisTotal synthesis of bryostatin 16 using atom-economical and chemoselective approachesRedox Economy in Organic SynthesisNucleophilic additions to tetrahydropyridinium salts. Applications to alkaloid synthesesTotal Synthesis of (±)‐Gephyrotoxin by Amide‐Selective Reductive Nucleophilic AdditionNew Method for Synthesis of Aldehydes from Esters by Sodium Diisobutyl-<i>t</i>-butoxyaluminum HydrideThioamides and Thioformamides for Sequential Reactions with Organolithium and Grignard ReagentsTotal syntheses of dl-gephyrotoxin and dl-dihydrogephyrotoxinAn efficient synthesis of substituted prolines by the selective reduction and reductive cyanation of 2-pyrrolidonesSynthetic applications of N-acylamino-1,3-dienes. 10. Importance of allylic interactions and stereoelectronic effects in dictating the steric course of the reaction of iminium ions with nucleophiles. An efficient total synthesis of (.+-.)-gephyrotoxinThree-component condensations of aldehydes with N-methoxycarboxamidesCu-Catalyzed Alkylation of Grignard Reagents: A New Efficient ProcedureThe Atom Economy—A Search for Synthetic EfficiencyA short total synthesis of (.+-.)-perhydrogephyrotoxinImproved Procedure for the Reductive Acetylation of Acyclic Esters and a New Synthesis of EthersChemical Synthesis of Natural Product Peptides: Coupling Methods for the Incorporation of Noncoded Amino Acids into PeptidesA Mild General Procedure for the One‐Pot Conversion of Amides to AldehydesRapid Assembly of Quinolizidines via Consecutive Nucleophilic Cyclizations onto Activated AmidesSynthesis of the Kopsia alkaloids (±)-11,12-demethoxylahadinine B, (±)-kopsidasine and (±)-kopsidasine-N-oxideGephyrotoxins, Histrionicotoxins and Pumiliotoxins from the Neotropical Frog <i>Dendrobates histrionicus</i>Chemoselective synthesis of ketones and ketimines by addition of organometallic reagents to secondary amidesChemoselectivity and the Curious Reactivity Preferences of Functional GroupsFunctionalized Aminocyclopropanes From Functionalized Organozinc Compounds and N,N-DialkylcarboxamidesFormal Total Synthesis of (+)-GephyrotoxinSynthesis of Benzo-Fused 1-Azabicyclo[<i>m</i>.<i>n</i>.0]alkanes via the Schmidt Reaction: A Formal Synthesis of GephyrotoxinNicotinic receptor-elicited sodium flux in rat pheochromocytoma PC12 cells: Effects of agonists, antagonists, and noncompetitive blockersReduction of Secondary Carboxamides to IminesPreparation of 2,6-disubstituted 2,3-Dihydro-4-pyridones: Dehydrogenation of trimethylsilyl enol ethers with palladium (ii) acetateAnalysis of organomagnesium and organolithium reagents using N-phenyl-1-naphthylamineTertiary amide-based Knoevenagel-type reactions: a direct, general, and chemoselective approach to enaminonesCyclizations of <i>N</i>-Acyliminium IonsN-methoxy-n-methylamides as effective acylating agentsComplete proton and carbon-13 NMR assignment of the alkaloid gephyrotoxin through the use of homonuclear Hartmann-Hahn and two-dimensional spectroscopyChemoselective Reduction of Esters to Aldehydes by Potassium Diisobutyl-t-butoxyaluminum Hydride (PDBBA)Convergent Synthesis of Polycyclic Ethers via the Intramolecular Allylation of α-Acetoxy Ethers and Subsequent Ring-Closing Metathesis: Synthesis of the CDEFG Ring System of GambierolEfficient generation and intramolecular cyclization reactions of acyl iminesA versatile two-step method for the reductive alkylation and formal [4 + 2] annulation of secondary lactams: step economical syntheses of the ant venom alkaloids (2R,5S)-2-butyl-5-propylpyrrolidine and (+)-monomorine I<i>Z</i>-Selective Horner−Wadsworth−Emmons Reaction of Ethyl (Diarylphosphono)acetates Using Sodium Iodide and DBUAsymmetric Total Synthesis of (−)-α-Kainic Acid Using an Enantioselective, Metal-Promoted Ene CyclizationSynthesis of (.+-.)-gephyrotoxinA Practical in situ Generation of the Schwartz Reagent. Reduction of Tertiary Amides to Aldehydes and HydrozirconationOrganocerium reactions of benzamides and thiobenzamides: A direct synthesis of tertiary carbinaminesA Direct and General Method for the Reductive Alkylation of Tertiary Lactams/Amides: Application to the Step Economical Synthesis of Alkaloid (−)-Morusimic Acid DGeneration of Secondary, Tertiary, and Quaternary Centers by Geminal Disubstitution of Carbonyl OxygensDirect Transformation of Secondary Amides into Secondary Amines: Triflic Anhydride Activated Reductive AlkylationTotal synthesis of (.+-.)-gephyrotoxinDirect Transformation of Amides into α-Amino Phosphonates <i>via</i> a Reductive Phosphination ProcessA Cascade Strategy Enables a Total Synthesis of (−)‐GephyrotoxinThe versatile conversion of acyclic amides to α-alkylated aminesA Novel and Expeditious Reduction of Tertiary Amides to Aldehydes Using Cp<sub>2</sub>Zr(H)ClA Direct Entry to Substituted <i>N</i>‐Methoxyamines from <i>N</i>‐Methoxyamides via <i>N</i>‐Oxyiminium IonsStereoselective total synthesis of (.+-.)-perhydrogephyrotoxin. Synthetic applications of directed 2-azonia-[3,3]-sigmatropic rearrangementsNew reactions and step economy: the total synthesis of (±)-salsolene oxide based on the type II transition metal-catalyzed intramolecular [4+4] cycloadditionAmide bond formation: beyond the myth of coupling reagentsIodine(III)-Mediated Cyclization of Unsaturated O-Alkyl Hydroxamates: Silyl-Assisted Access to α-Vinyl and α-(2-Silylvinyl) LactamsDirect, One‐pot Sequential Reductive Alkylation of Lactams/Amides with Grignard and Organolithium Reagents through Lactam/Amide ActivationPharmacological activity of alkaloids from poison-dart frogs (dendrobatidae)Application of the Swern oxidation to the manipulation of highly reactive carbonyl compoundsGeneral Synthesis of α-Acetoxy Ethers from Esters by DIBALH Reduction and AcetylationClassification of skin alkaloids from neotropical poison-dart frogs (dendrobatidae)Mild and Selective Hydrozirconation of Amides to Aldehydes Using Cp<sub>2</sub>Zr(H)Cl: Scope and Mechanistic InsightMulticomponent Synthesis of α-Branched AmidesNEW TRENDS IN PEPTIDE COUPLING REAGENTSTotal Synthesis of (−)-Nakadomarin AStereodivergent Synthesis of Substituted N,O‐Containing Bicyclic Compounds by Sequential Addition of Nucleophiles to <i>N</i>‐AlkoxybicyclolactamsSynthesis of the Kopsia alkaloids (±)-pauciflorine B, (±)-lahadinine B, (±)-kopsidasine, (±)-kopsidasine-N-oxide, (±)-kopsijasminilam and (±)-11-methoxykopsilongineStereospecific total synthesis of (.+-.)-gephyrotoxin 223ABVersatile and Direct Transformation of Secondary Amides into Ketones by Deaminative Alkylation with Organocerium ReagentsA new approach to gephyrotoxinSynthesis of Tertiary <i>sec</i>‐Alkylamines by the Addition of Grignard Reagents to <i>N</i>,<i>N</i>‐Dialkylformamides Mediated by Ti(O<i>i</i>Pr)<sub>4</sub> and Me<sub>3</sub>SiClA Concise and Versatile Double‐Cyclization Strategy for the Highly Stereoselective Synthesis and Arylative Dimerization of Aspidosperma AlkaloidsHydrozirconation. Organic synthesis via organozirconium intermediates. Synthesis and rearrangement of alkylzirconium(IV) complexes and their reaction with electrophilesAmide bond formation and peptide couplingHydrido complexes of zirconium I. PreparationReductive deoxygenation by Cp2ZrHCl: Selective formation of imines via zirconation/hydrozirconation of amidesConverting Cycloalkanones into<i>N</i>-Heterocycles: Formal Synthesis of (−)-Gephyrotoxin 287CHighly efficient synthesis of aldenamines from carboxamides by iridium-catalyzed silane-reduction/dehydration under mild conditionsA Modified Bouveault Reaction for the Preparation of α,α-Dimethylamines from AmidesA novel method for the formation of N-glycosides using hydroxamateSynthesis of Tertiary Propargylamines by Sequential Reactions of in Situ Generated Thioiminium Salts with Organolithium and -magnesium ReagentsA Rapid and Simple Cleanup Procedure for Metathesis ReactionsA new stereoselective synthesis of (.+-.)-perhydrogephyrotoxin.
- 連携機関・データベース
- 国立情報学研究所 : CiNii Research
- 提供元機関・データベース
- Japan Link Center雑誌記事索引データベース雑誌記事索引データベースCrossrefCiNii Articles科学研究費助成事業データベースCrossrefCrossrefCrossrefCrossrefCrossrefCrossrefCrossrefCrossrefCrossref
- 書誌ID（NDLBibID）
- 02632213911343187
- NII論文ID
- 130005064992