A Facile Synthesis of Optically Pure (−)‐( S )‐Ipsenol Using a Chiral Titanium Complex | Zendy

Oertle Konrad | Zendy; Beyeler Harry | Zendy; Duthaler Rudolf O. | Zendy; Lottenbach Willi | Zendy; Riediker Martin | Zendy; Steiner Eginhard | Zendy

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A Facile Synthesis of Optically Pure (−)‐( S )‐Ipsenol Using a Chiral Titanium Complex

Author(s) -

Oertle Konrad,

Beyeler Harry,

Duthaler Rudolf O.,

Lottenbach Willi,

Riediker Martin,

Steiner Eginhard

Publication year - 1990

Publication title -

helvetica chimica acta

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.74

H-Index - 82

eISSN - 1522-2675

pISSN - 0018-019X

DOI - 10.1002/hlca.19900730215

Subject(s) - chemistry , enantioselective synthesis , aldol reaction , carboxylate , moiety , titanium , optically active , diene , stereochemistry , pheromone , combinatorial chemistry , organic chemistry , catalysis , botany , natural rubber , biology

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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