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Total synthesis of Junionone, a natural monoterpenoid from Juniperus communis L., and determination of the absolute configuration of the naturally occurring enantiomer by ROA spectroscopy

Lovchik, Martin A. ; Fráter, Georg ; Goeke, Andreas ; Hug, Werner

In: Chemistry & Biodiversity, 2008, vol. 5, no. 1, p. 126-139

Recently, we reported a novel access to 2,2-diethyl-3-[(E/Z)-prop-1-en-1-yl]cyclobutanone by an intramolecular nucleophilic substitution with allylic rearrangement (SNi′) of (E)-6-chloro-3,3-diethylhept-4-en-2-one. The ring closure reaction was found to proceed with selective syn-displacement of the leaving group. This method was now applied...