A Facile Synthesis of Optically Pure (−)‐( S )‐Ipsenol Using a Chiral Titanium Complex
1990; Wiley; Volume: 73; Issue: 2 Linguagem: Inglês
10.1002/hlca.19900730215
ISSN1522-2675
AutoresKonrad Oertle, Harry Beyeler, Rudolf O. Duthaler, Willi Lottenbach, Martin Riediker, E. Steiner,
Tópico(s)Synthetic Organic Chemistry Methods
ResumoAbstract A stereocontrolled synthetic route to optically pure (−)‐( S )‐ipsenol ( 1 ), 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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