Synthesis and absolute stereochemistry of spiroacetals in rove beetles (Coleoptera: Staphylinidae)

✍ Scribed by Hesheng Zhang; Mary T. Fletcher; Konrad Dettner; Wittko Francke; William Kitching

• Book ID: 104262390
• Publisher: Elsevier Science
• Year: 1999
• Tongue: French
• Weight: 196 KB
• Volume: 40
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(99)01612-3

✦ Synopsis

The unusual branched-carbon chain spiroacetal, 2,2,8-trimethyl-1,7-dioxaspiro[5.5]undecane, has been synthesised as its racemate and (6S,8R)-isomer. The natural compound, identified in the rove beetle, Ontholestes murinus (L.) proved to be the (6R,8S)-isomer. (E,E)-2,8-Dimethyi-1,7-dioxaspiro[5.5]undecane, a major component of the volatiles from the same insect, is the (2S,6R,8S)-isomer, but is largely racemic in Ontholestes tesselatus (Geoffr. Fourcr.).