Bioorganic & Medicinal Chemistry 1996-03-01

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

Index: Bioorg. Med. Chem. 4(3) , 363-74, (1996)

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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.

Structure	Name/CAS No.	Molecular Formula	Articles
	2,5,5-TRIMETHYL-2-(2-BROMOETHYL)-1,3-DIOXANE CAS:87842-52-2	C₉H₁₇BrO₂

J.C. Stowell et al.
[Organic Synth. 62 , 140, (1984)]

B.B. Snider, C.P. Cartaya-Marin
[J. Org. Chem. 49 , 153, (1984)]

The Total synthesis of (+)-artemisinin and (+)-9-desmethylte...
[Tetrahedron Lett. 28(4) , 4629-32, (1987)]

Reductive Cyclization of (3-) and (4-Oxoalkyl)-9, 10-anthraq...
[J. Prakt. Chem./Chem.-Ztg. 340(1) , 26-33, (1998)]

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

Abstract

Related Compounds