A simple synthesis of (−)-( R)-ipsdienol and (−)-( S)-ipsenol

A short and efficient synthesis of the unnatural enantiomer of (+)-( S)-ipsdienol 1 and (−)-( S)-ipsenol 2 is presented via an asymmetric allylboration. The synthesis was achieved by using a one-pot reduction–methylenation of an exo-methylene lactone intermediate.

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Bibliographic Details
Published inTetrahedron: asymmetry Vol. 10; no. 22; pp. 4281 - 4284
Main Authors Draillard, Karine, Lebreton, Jacques, Villiéras, Jean
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 19.11.1999
Elsevier
Subjects
Chemistry
Chemistry, Inorganic & Nuclear
Chemistry, Organic
Chemistry, Physical
Physical Sciences
Science & Technology
CONVENIENT ROUTE
ALCOHOLS
IPS BARK BEETLES
IPSDIENOL
ASYMMETRIC-SYNTHESIS
PHEROMONE SYNTHESIS
ENANTIOMERS
ALDEHYDES
STEREOSELECTIVE SYNTHESIS
IPSENOL
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Summary:A short and efficient synthesis of the unnatural enantiomer of (+)-( S)-ipsdienol 1 and (−)-( S)-ipsenol 2 is presented via an asymmetric allylboration. The synthesis was achieved by using a one-pot reduction–methylenation of an exo-methylene lactone intermediate.
ISSN:0957-4166
1362-511X
DOI:10.1016/S0957-4166(99)00482-6