• Medientyp: E-Artikel
  • Titel: Asymmetric Formal Synthesis of Azadirachtin
  • Beteiligte: Mori, Naoki; Kitahara, Takeshi; Mori, Kenji; Watanabe, Hidenori
  • Erschienen: Wiley, 2015
  • Erschienen in: Angewandte Chemie
  • Sprache: Deutsch
  • DOI: 10.1002/ange.201507935
  • ISSN: 0044-8249; 1521-3757
  • Schlagwörter: General Medicine
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  • Beschreibung: <jats:title>Abstract</jats:title><jats:p>An asymmetric formal synthesis of azadirachtin, a potent insect antifeedant, was accomplished in 30 steps to Ley’s synthetic intermediate (longest linear sequence). The synthesis features: 1) rapid access to the optically active right‐hand segment starting from the known 5‐hydroxymethyl‐2‐cyclopentenone scaffold; 2) construction of the B and E rings by a key intramolecular tandem radical cyclization; 3) formation of the hemiacetal moiety in the C ring through the α‐oxidation of the six‐membered lactone followed by methanolysis.</jats:p>