Identification and synthesis of new bicyclic acetals from the mountain pine beetle, Dendroctoaus ponderosae Hopkins (Col: Scol)
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| Authors: | Francke, W; Schroder, F; Philipp, P; Meyer, H; Sinnwell, V; Gries, G |
| Year: | 1996 |
| Journal: | Bioorganic & Medicinal Chemistry 4: 363-374 |
| Title: | Identification and synthesis of new bicyclic acetals from the mountain pine beetle, Dendroctoaus ponderosae Hopkins (Col: Scol) |
| Abstract: | Head-space volatiles obtained from male mountain pine beetles, Dendroctonus ponderosae, were analyzed by coupled CC-MS and chiral gas chromatography. 5-Ethyl-7-methyl-6,8-dioxabicyclo[3.2.1] (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] (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. Copyright (C) 1996 Elsevier Science Ltd |
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