A convenient synthesis of 6-hydroxy-7,9-bis(p-methoxybenzyl)-5-methylene-2-oxa-7,9-diazabicyclo(4.2.2)decane-8,10-dione.
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概要
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The title compound, the key intermediate for a total synthesis of bicyclomycin, was synthesized from <I>N</I>,<I>N</I>′-diacetyl anhydroglycine through twelve steps. The three-carbon branch for the construction of the bicyclic skeleton was introduced to the 2,5-piperazinedione ring as an alkylidene substituent, and then the olefinic function was converted into a diol function. The formation of bicyclic ring was achieved by treatment with <I>N</I>-bromosuccinimide followed by the intramoleculer substitution of the primary hydroxyl group in the side chain, and finally the secondary hydroxyl group was converted to the methylene function by an improved Peterson reaction.
- 公益社団法人 日本化学会の論文
著者
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Yoshimura Juji
Laboratorium für Organische Chemie Technische Hochschule Tokyo
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Yamaura Masanori
Laboratory of Chemistry for Natural Products, Faculty of Science, Tokyo Institute of Technology
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Shin Chung-gi
Laboratory of Chemistry for Natural Products, Faculty of Science, Tokyo Institute of Technology
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Hashimoto Hironobu
Laboratory for Chemistry of Natural Products, Faculty of Science
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Suzuki Tsuneji
Laboratory of Chemistry for Natural Products, Faculty of Science, Tokyo Institute of Technology
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- Dehydrooligopeptides. III. Synthesis of (Z,Z)- and (Z,E)-geometric isomers of dehydrodipeptides and their base-catalyzed transformation to the hydantoin derivatives.
- The confirmation of the configuration of ethyl 2-bromo-3-nitro-2-alkenoate by 13C NMR spectroscopy.
- Asymmetric Reactions. VI. Asymmetric Hydrogenation of Atropate Catalyzed by Cyanocobalt-Opticall Active Diamine Complex
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- Preparations and properties of optically active (alkyl)bis(dimethylglyoximato)cobalt(III) complexes.
- Asymmetric Hydrogenation Catalyzed by Bis(dimethylglyoximato)cobalt(II)-Optically Active Amine Complex
- .ALPHA.,.BETA.-Unsaturated carboxylic acid derivatives. XVII. The facile synthesis of ethyl .ALPHA.-azido-.ALPHA.-alkenoates and reduction to ethyl .ALPHA.-amino-.ALPHA.-alkenoates.
- .ALPHA.,.BETA.-Unsaturated carboxylic acid derivatives. XIV. The synthesis and reduction of Diels-Alder adducts from ethyl 3-nitro-2-alkenoates and cyclopentadiene.
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- .ALPHA.,.BETA.-Unsaturated carboxylic acid derivatives. XXI. A novel synthesis of .ALPHA.-dehydroamino acid derivatives by the Arbusov reaction of .ALPHA.-phosphoranylideneamino-2-alkenoates.
- Dehydrooligopeptides. II. The synthesis of dehydrodehydrodipeptides by direct coupling and base-catalyzed .BETA.-elimination.
- A Novel Synthesis of Ethyl β-Diethoxyphosphinyl-α,β-unsaturated-carboxylates
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- Branched-chain sugars. V. Stereoselective synthesis of 3-C- and 5-C-methyl-D-glucoses, and 5-C-methyl-L-idose derivatives.
- The Synthesis and Reaction of α,β-Unsaturated α-Nitrocarboxylic Esters
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- Aminosugars. XXIII. L-Idofuranose Derivatives Containing a Heterocycle at C-5,6 Position
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- Branched-chain Sugars. III. Addition of Vinylmagnesium Bromide to 5,6-Dideoxy-1,2-O-isopropylidene-6-C-nitro-3-O-substituted-α-D-xylo-hex-5-enof uranoses
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- The Reaction of β-Nitroalcohols and Reactive Aldehydes
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- α,β-Unsaturated Carboxylic Acid Derivatives. IX. The Cyclization of α-(N-Acyl-hydroxyamino) Acid Esters with Ammonia or Hydroxylamine
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- Asymmetric reactions. X. Asymmetric hydrogenation catalyzed by bis(dimethylglyoximato)cobalt(II)-chiral cocatalyst (amino alcohol) system.
- α,β-Unsaturated Carboxylic Acid Derivatives. VI. New Synthesis of N-Acyl-α-dehydroamino Acid Esters
- α,β-Unsaturated Carboxylic Acid Derivatives. X. The Synthesis and Reaction of α-Azido-diethoxyphosphinyl-α- and β-alkenes
- Studies on Nitro Carboxylic Acids. III. The Reaction of α-Nitroolefins with Triethyl or Diethyl Phosphite
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- .ALPHA.,.BETA.-Unsaturated carboxylic acid derivatives. XI. Convenient synthesis of tert-butyl 2-alkoxy- and hydroxy-2-acetylamino-3-mono- or 3,3-dihaloalkanoates.
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- Convenient synthesis of 3-aminocoumarin derivatives by the condensation of 1,4-diacetyl-or 3-substituent-2,5-piperazinediones with various salicylaldehyde derivatives.
- The Reaction of α-Oxo Acids with N-Phenyltriphenylphosphinimine