Identification and synthesis of new bicyclic acetals from the mountain pine beetle, Dendroctonus ponderosae Hopkins (Col.: Scol.)

W Francke; F Schröder; P Philipp; H Meyer; V Sinnwell; G Gries

doi:10.1016/0968-0896(96)00013-2

Identification and synthesis of new bicyclic acetals from the mountain pine beetle, Dendroctonus ponderosae Hopkins (Col.: Scol.)

Bioorg Med Chem. 1996 Mar;4(3):363-74. doi: 10.1016/0968-0896(96)00013-2.

Authors

W Francke¹, F Schröder, P Philipp, H Meyer, V Sinnwell, G Gries

Affiliation

¹ Institut für Organische Chemie der Universität, Hamburg, Germany.

PMID: 8733614
DOI: 10.1016/0968-0896(96)00013-2

Abstract

Head-space volatiles obtained from male mountain pine beetles, Dendroctonus ponderosae, were analyzed by coupled GC-MS and chiral gas chromatography. 5-Ethyl-7-methyl-6,8-dioxabicyclo[3.2.1]octane (6) was found as a new naturally occurring isomer of brevicomin (1). In addition, several stereoisomers of 7-ethyl-5-methyl-6,8-dioxabicyclo[3.2.1]octan-2-ol (11) and 1-(5-methyl-6,8-dioxabicyclo[3.2.1]octyl)ethanol (12) could be identified. Relative and absolute configurations of the compounds were determined by unambiguous syntheses, which are described.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Animals
Bridged Bicyclo Compounds, Heterocyclic / analysis*
Bridged Bicyclo Compounds, Heterocyclic / chemical synthesis
Coleoptera / chemistry*
Gas Chromatography-Mass Spectrometry
Magnetic Resonance Spectroscopy
Male
Sex Attractants / analysis*
Sex Attractants / chemical synthesis
Stereoisomerism

Substances

Bridged Bicyclo Compounds, Heterocyclic
Sex Attractants
brevicomin