(1R,2S,6R)-2-Hydroxymethyl-2,6-dimethyl-3-oxabicyclo[4.2.0]octane, a new volatile released by males of the papaya borer Pseudopiazurus obesus (Col.: Curculionidae)

Paulo H G Zarbin; Marcos A B Moreira; Jenny Haftmann; Armin Tröger; Stephan Franke; Jürgen Kopf; Kenji Mori; Wittko Francke

doi:10.1021/ol100074q

(1R,2S,6R)-2-Hydroxymethyl-2,6-dimethyl-3-oxabicyclo[4.2.0]octane, a new volatile released by males of the papaya borer Pseudopiazurus obesus (Col.: Curculionidae)

Org Lett. 2010 Jun 4;12(11):2447-9. doi: 10.1021/ol100074q.

Authors

Paulo H G Zarbin¹, Marcos A B Moreira, Jenny Haftmann, Armin Tröger, Stephan Franke, Jürgen Kopf, Kenji Mori, Wittko Francke

Affiliation

¹ Department of Chemistry, Federal University of Parana, 81531-990, Curitiba-PR, Brazil.

PMID: 20465270
DOI: 10.1021/ol100074q

Abstract

Sex-specific volatiles produced by males of the papaya beetle Pseudopiazurus obesus are (1R,2S)-grandisal (1), (1R,2S)-grandisol (2), and the new (1R,2S,6R)-2-hydroxymethyl-2,6-dimethyl-3-oxabicyclo[4.2.0]octane (3) termed papayanol.

MeSH terms

Animals
Bridged Bicyclo Compounds, Heterocyclic / chemistry
Bridged Bicyclo Compounds, Heterocyclic / isolation & purification*
Bridged Bicyclo Compounds, Heterocyclic / pharmacology*
Carica / parasitology*
Coleoptera / chemistry*
Male
Molecular Structure
Nuclear Magnetic Resonance, Biomolecular
Sex Attractants / chemistry
Sex Attractants / isolation & purification*
Sex Attractants / pharmacology*
Stereoisomerism
Terpenes / chemistry
Terpenes / pharmacology

Substances

(1R,2S,6R)-2-hydroxymethyl-2,6-dimethyl-3-oxabicyclo(4.2.0)octane
Bridged Bicyclo Compounds, Heterocyclic
Sex Attractants
Terpenes
grandisol