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Pheromone Synthesis, CXVI Conversion of the Enantiomers of Sulcatol to the Enantiomers of cis ‐Pityol, a Volatile Compound from the Elm Bark Beetle Pteleobius vittatus
Author(s) -
Mori Kenji,
Puapoomchareon Prapai
Publication year - 1989
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.1989198902100
Subject(s) - chemistry , enantiomer , bark beetle , pheromone , catalysis , stereochemistry , bark (sound) , organic chemistry , botany , biology , physics , acoustics
Pure cis ‐(2 R ,5 R )‐pityol ( 1 ) was synthesized from ethyl ( R )‐3‐hydroxybutanoate ( 3 ) via cyclization of ( R )‐sulcatol ( 2 ) with tert ‐butyl hydroperoxide in the presence of a vanadium catalyst. In the same manner, cis ‐(2 S ,5 S )‐pityol ( 1 ) was synthesized from ( S )‐ 3 via ( S )‐ 2 .