Highly efficient stereoselective syntheses of both (Z)- and (E)-γ-bisabolenes (1) were achieved by ring closing metathesis of stereodefined tetrasubstituted alkenes. Both (Z)- and (E)-tetrasubstituted alkene precursors were obtained by Cu-catalyzed stereoselective addition of allylmagnesium bromide to propargyl alcohols, followed by Pd-catalyzed cross coupling of alkylzinc derivatives. This represents the first application of ring-closing metathesis to the stereoselective synthesis of exocyclic alkenes.
|Number of pages||5|
|Journal||European Journal of Organic Chemistry|
|Publication status||Published - 2001|
- Asymmetric synthesis
- Natural products
ASJC Scopus subject areas
- Organic Chemistry