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Mori, Kenji; Amaike, Masayasu; Watanabe, Hidenori

Pheromone Synthesis, CLVIII. New Synthesis and Revision of the Absolute Configuration of the Hemiacetal Pheromone of the Spined Citrus Bug Biprorulus bibax

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  • Medientyp: E-Artikel
  • Titel: Pheromone Synthesis, CLVIII. New Synthesis and Revision of the Absolute Configuration of the Hemiacetal Pheromone of the Spined Citrus Bug Biprorulus bibax
  • Beteiligte: Mori, Kenji; Amaike, Masayasu; Watanabe, Hidenori
  • Erschienen: Wiley, 1993
  • Erschienen in: Liebigs Annalen der Chemie
  • Sprache: Englisch
  • DOI: 10.1002/jlac.1993199301210
  • ISSN: 0170-2041
  • Schlagwörter: Organic Chemistry ; Physical and Theoretical Chemistry
  • Entstehung:
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  • Beschreibung: <jats:title>Abstract</jats:title><jats:p>The enantiomers and the racemate of (3<jats:italic>R</jats:italic>,4<jats:italic>S</jats:italic>,1′<jats:italic>E</jats:italic>)‐3,4‐bis(1′‐butenyl)tetrahydro‐2‐furanol (<jats:bold>1</jats:bold>) were synthesized by employing Ireland's ester enolate Claisen rearrangement of <jats:bold>5</jats:bold> as the key reaction to provide the corresponding lactone <jats:bold>3</jats:bold> via <jats:bold>4</jats:bold>. Optically active <jats:bold>3</jats:bold> was prepared by employing either chemical asymmetric reduction [<jats:bold>12</jats:bold> → (<jats:italic>S</jats:italic>)‐<jats:bold>8b</jats:bold>] or lipase‐mediated asymmetric hydrolysis (<jats:bold>9</jats:bold>→<jats:bold>10</jats:bold>) and acetylation (<jats:italic>meso</jats:italic>‐<jats:bold>2</jats:bold> → <jats:italic>ent</jats:italic>‐<jats:bold>10</jats:bold>) as the key transformations. The absolute configuration of the naturally occurring <jats:bold>1</jats:bold> was revised as (3<jats:italic>R</jats:italic>,4<jats:italic>S</jats:italic>) on the basis of the chemical asymmetric synthesis of (3<jats:italic>S</jats:italic>,4<jats:italic>R</jats:italic>)‐<jats:bold>3</jats:bold> by starting from (<jats:italic>S</jats:italic>)‐<jats:bold>8b</jats:bold> of known stereochemistry.</jats:p>