Helvetica Chimica Acta p. 353 - 358 (1990)
Update date:2022-08-11
Topics:
Oertle, Konrad
Beyeler, Harry
Duthaler, Rudolf O.
Lottenbach, Willi
Riediker, Martin
Steiner, Eginhard
A stereocontrolled synthetic route to optically pure (-)-(S)-ipsenol (I), the pheromone of Pityokteines curvidens and various other bark-beetle species is described.Key step of the synthesis is an enantioselective aldol reaction using a chiral titanium-carbohydrate complex (Scheme 1).The carboxylate function of the optically pure β-hydroxy acid 5 thus obtained in mol quantities is then elaborated to the diene moiety by standard methodology (Scheme 2).
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