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Muto, Shin‐etsu; Bando, Masahiko; Mori, Kenji

Synthesis and Stereochemistry of the Four Himachalene‐Type Sesquiterpenes Isolated from the Flea Beetle (Aphthona flava) as Pheromone Candidates

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  • Medientyp: E-Artikel
  • Titel: Synthesis and Stereochemistry of the Four Himachalene‐Type Sesquiterpenes Isolated from the Flea Beetle (Aphthona flava) as Pheromone Candidates
  • Beteiligte: Muto, Shin‐etsu; Bando, Masahiko; Mori, Kenji
  • Erschienen: Wiley, 2004
  • Erschienen in: European Journal of Organic Chemistry
  • Sprache: Englisch
  • DOI: 10.1002/ejoc.200300812
  • ISSN: 1434-193X; 1099-0690
  • Schlagwörter: Organic Chemistry ; Physical and Theoretical Chemistry
  • Entstehung:
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  • Beschreibung: <jats:title>Abstract</jats:title><jats:p>Both the (1<jats:italic>S</jats:italic>,2<jats:italic>R</jats:italic>) and (1<jats:italic>R</jats:italic>,2<jats:italic>S</jats:italic>) isomers of 2,6,6‐trimethylbicyclo[5.4.0]undec‐7‐en‐9‐one (<jats:bold>1</jats:bold>) were synthesized by starting from (<jats:italic>S</jats:italic>)‐ and (<jats:italic>R</jats:italic>)‐citronellal (<jats:bold>5</jats:bold>), respectively. The stereochemistry of (1<jats:italic>R</jats:italic>,2<jats:italic>S</jats:italic>)‐(−)‐<jats:bold>1</jats:bold> was established by an X‐ray analysis; it exhibits a CD spectrum similar to that of cholest‐4‐en‐3‐one, in agreement with its absolute configuration. The ketones (1<jats:italic>S</jats:italic>,2<jats:italic>R</jats:italic>)‐ and (1<jats:italic>R</jats:italic>,2<jats:italic>S</jats:italic>)‐<jats:bold>1</jats:bold> were converted into the enantiomers of three other himachalene hydrocarbons, 2,2,6‐trimethyl‐10‐methylenebicyclo[5.4.0]undec‐1(11)‐ene (<jats:bold>2</jats:bold>), 1,1,5,8‐tetramethyl‐1,2,3,4,5,6,5a‐heptahydrobenzo[1,2‐<jats:italic>a</jats:italic>][7]annulene (<jats:bold>3</jats:bold>), and 1,1,5,8‐tetramethyl‐1,2,3,4,5‐pentahydrobenzo[<jats:italic>a</jats:italic>][7]annulene (<jats:italic>ar</jats:italic>‐himachalene, <jats:bold>4</jats:bold>). The stereochemistry of these himachalene‐type sesquiterpenes isolated from flea beetles such as <jats:italic>Aphthona flava</jats:italic> and <jats:italic>Phyllotreta cruciferae</jats:italic> as their male‐pheromone components was revised to (1<jats:italic>S</jats:italic>,2<jats:italic>R</jats:italic>)‐<jats:bold>1</jats:bold>, (6<jats:italic>R</jats:italic>,7<jats:italic>S</jats:italic>)‐<jats:bold>2</jats:bold>, (5<jats:italic>R</jats:italic>,5a<jats:italic>S</jats:italic>)‐<jats:bold>3</jats:bold>, and (<jats:italic>R</jats:italic>)‐<jats:bold>4</jats:bold>. (© Wiley‐VCH Verlag GmbH &amp; Co. KGaA, 69451 Weinheim, Germany, 2004)</jats:p>