.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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概要

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• The Diels-Alder reactions of cyclopentadiene with ethyl (<I>E</I>)- and (<I>Z</I>)-3-nitrocrotonate were carried out to give only the (2+4)-nitro adduct as a mixture of three diastereomers, while that of the diene with ethyl (<I>Z</I>)-3-nitrocinnamate gave two kinds of cycloaddition products, (2+2)- and (2+4)-nitro adducts. All the nitro adducts were reduced with aluminum-amalgam to give the corresponding mono- and dihydroxyamino compounds, in which vicinal <I>endo</I>-ethoxycarbonyl-<I>endo</I>-hydroxyamino derivatives cyclized readily to give tricyclic compounds containing isoxazolidinone ring. The stereochemistry of all the new compounds were established on the basis of IR and NMR spectroscopic analyses.

• 公益社団法人 日本化学会の論文

著者

• Shin Chung-gi

  Laboratory Of Oraganic Chemistry Faculty Of Engineering Kanagawa University

• Yoshimura Juji

  Laboratorium für Organische Chemie Technische Hochschule Tokyo

• Yamaura Masanori

  Laboratory of Chemistry for Natural Products, Faculty of Science, Tokyo Institute of Technology

• Yamaura Masanori

  Laboratory of Organic Chemistry, Faculty of Technology, Kanagawa University

• Kosuge Yasuhiro

  Laboratory of Organic Chemistry, Faculty of Technology, Kanagawa University

• Shin Chung-gi

  Laboratory of Chemistry for Natural Products, Faculty of Science, Tokyo Institute of Technology

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