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Stereospezifische Synthese von (+)‐(3 R , 4 R )‐4‐Methyl‐3‐heptanol, das Enantiomere eines Pheromons des kleinen Ulmensplintkäfers ( Scolytus multistriatus )
Author(s) -
Fráter György
Publication year - 1979
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.19790620833
Subject(s) - chemistry , stereospecificity , stereochemistry , ether , enantiomer , bark beetle , alcohol , medicinal chemistry , organic chemistry , catalysis , bark (sound) , physics , acoustics
Stereospecific Synthesis of (+)‐(3 R , 4 R )‐4‐Methyl‐3‐heptanol, the Enantiomer of a Pheromone of the Smaller European Elm Bark Beetle ( Scolytus multistriatus ) Reduction of 2 with actively fermenting baker's yeast gave (−) ‐3. Stereospecific alkylation [3] of (−) ‐3 with propyl iodide furnished ethyl (+)‐(2 R , 3 R )‐2‐propyl‐3‐hydroxypentanoate ((+) ‐4 , 58%) which was converted to the tetrahydropyranyl ether (−) ‐5 , then the alcohol 6 , the p ‐toluenesulfonate 7 and the thiophenyl ether 8 to give the title compound (+) ‐1. The latter consisted of 97% of the threo ‐ and 3% of the erythro ‐isomer. The above synthesis also correlates the absolute configuration of (−)‐( R ) ‐3 with that of (+)‐( R )‐citronellic acid (see [2]).