Syntheses of the female sex pheromones of Matsucoccus pine scales using the [2,3]-wittig rearrangement of a bisallylic tertiary ether

Abstract A convergent, general synthesis of (2E,4E)-4,6,10,12-tetramethyltrideca-2,4-dien-7-one (matsuone, 1) and five closely related analogs (2–6), which serve as sex pheromone components of female Matsucoccus pine scales, is described. The aldehydes 8a and 8b were obtained via a reaction sequence in which the key step is a [2,3]-Wittig sigmatropic rearrangement of the oxazoline ether of bisallylic tertiary alcohol 11. Coupling of 8 with the appropriate nucleophilic reagents, followed by oxidation of the resultant secondary alcohols, afforded the pheromone components 1–6.

• Publication year

  1995

• Venue

  Tetrahedron

• Publication date

  1995-09-18

• Fields of study

  Chemistry

• Identifiers
  DOI 10.1016/0040-4020(95)00622-F
• External record

  Open on Semantic Scholar

• Source metadata

  Semantic Scholar

• No claims are published for this paper.

• No concepts are published for this paper.

• Identification of the female sex pheromone of the Israeli pine bast scale Matsucoccus josephi.

  1993cited by this paper
• Synthesis and field bioassay of the Israeli pine bast scale, Matsucoccus josephi, female sex pheromone

  1993cited by this paper
• Enantioselective synthesis of all four stereoisomers of (2E, 4E)-4,6,10,12-tetramethyl-2,4-tridecadien-7-one, the sex pheromone of Matsucoccus pine bast scale

  1993cited by this paper
• Enantioselective synthesis of a sex attractant pheromone of the pine scale Matsucoccus feytaudi.

  1991cited by this paper
• Synthesis of (-)-(6R,10R)-matsuone. Assignment of relative stereochemistry to a pheromone of Matsucoccus pine bast scales

  1991cited by this paper
• Assignment of (6R*,10R*)-relative stereochemistry to the major component of the sex pheromone of the maritime pine scale, matsucoccus feytaudi

  1991cited by this paper
• Identification of the sex pheromone of the maritime pine scale

  1990cited by this paper
• [2,3]-Wittig sigmatropic rearrangements in organic synthesis

  1986cited by this paper
• Synthesis of 2‐(α‐hydroxyalkyl)‐1,3‐heterocyclic alcohols and aryl carbamates

  1983cited by this paper
• Conversion of allylic alcohols to chlorides without rearrangement

  1972cited by this paper

• A Polyketide Male-Produced Aggregation-Sex Pheromone Shared by the North American Cerambycid Beetle Graphisurus fasciatus and the South American Cerambycid Eutrypanus dorsalis

  2024cites this paper
• Development of a pheromone trap for monitor black pine bast scale, Matsucoccus thunbergianae (Hemiptera: Margarodidae)

  2016cites this paper
• Chemistry of the pheromones of mealybug and scale insects.

  2015cites this paper
• One or More CH and/or CC Bond(s) Formed by Rearrangement

  2005cites this paper
• Syntheses of the Female Sex Pheromones of Matsucoccus Pine Scales Using the (2,3)-Wittig Rearrangement of a Bisallylic Tertiary Ether.

  1996cites this paper