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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 ).