• Medientyp: E-Artikel
  • Titel: Synthesis of (±)‐4‐Demethoxydaunomycinone by Double Diels‐Alder Additions to 2, 3, 5, 6‐Tetramethylidene‐7‐oxanorbornane
  • Beteiligte: Bessière, Yvonne; Vogel, Pierre
  • Erschienen: Wiley, 1980
  • Erschienen in: Helvetica Chimica Acta
  • Sprache: Englisch
  • DOI: 10.1002/hlca.19800630123
  • ISSN: 0018-019X; 1522-2675
  • Schlagwörter: Inorganic Chemistry ; Organic Chemistry ; Physical and Theoretical Chemistry ; Drug Discovery ; Biochemistry ; Catalysis
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  • Beschreibung: <jats:title>Abstract</jats:title><jats:p>Sequential <jats:italic>Diels‐Alder</jats:italic> additions of methylvinyl ketone and dehydrobenzene to 2, 3, 5, 6‐tetramethylidene‐7‐oxanorbornane <jats:bold>(4)</jats:bold> yielded the (5, 12‐epoxy‐1, 2, 3, 4, 5, 6, 11, 12‐octahydro‐2‐naphtacenyl) methyl ketone <jats:bold>(10)</jats:bold> which, in few steps was oxidized to a precursos of (±)‐4‐demethoxydaunomycinone. The preparations of two precursors of anthracyclinones, the (5‐acetoxy‐) and (12‐acetoxy‐1, 2, 3, 4‐tetrahydro‐2‐naphtacenyl) methyl ketones <jats:bold>(14, 15)</jats:bold> are presented. The synthesis of 6, 13‐epoxy‐6, 13‐dihydropentacene <jats:bold>(8)</jats:bold> is also reported.</jats:p>