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

被引：60

作者：

Francke, W

Schroder, F

Philipp, P

Meyer, H

Sinnwell, V

Gries, G

机构：

[1] UNIV HAMBURG,INST ORGAN CHEM,D-20146 HAMBURG,GERMANY

[2] SIMON FRASER UNIV,DEPT BIOL SCI,CTR PEST MANAGEMENT,BURNABY,BC V5A 1S6,CANADA

来源：

BIOORGANIC & MEDICINAL CHEMISTRY | 1996年 / 4卷 / 03期

关键词：

bicyclic acetals; 5-ethyl-7-methyl-6,8-dioxabicyclo[3.2.1]octane; hydroxybrevicomin; Dendroctonus ponderosae;

D O I：

10.1016/0968-0896(96)00013-2

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

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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页码：363 / 374

页数：12

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