Identification and synthesis of new bicyclic acetals from the mountain pine beetle, Dendroctonus ponderosae Hopkins (Col.: Scol.).
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.
Francke
W
W
Institut für Organische Chemie der Universität, Hamburg, Germany.
Schröder
F
F
Philipp
P
P
Meyer
H
H
Sinnwell
V
V
Gries
G
G
D000818:Animals; D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000032:analysis* / Q000138:chemical synthesis; D001517:Coleoptera / Q000737:chemistry*; D008401:Gas Chromatography-Mass Spectrometry; D009682:Magnetic Resonance Spectroscopy; D008297:Male; D012724:Sex Attractants / Q000032:analysis* / Q000138:chemical synthesis; D013237:Stereoisomerism
D019086:Bridged Bicyclo Compounds, Heterocyclic; D012724:Sex Attractants; C012219:brevicomin