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Pheromone Synthesis, XCVIII. Conversion of the Enantiomers of Sulcatol (6‐Methyl‐5‐hepten‐2‐ol) to the Enantiomers of Pityol [ trans ‐2‐(1‐Hydroxy‐1‐methylethyl)‐5‐methyltetrahydrofuran], a Male‐Specific Attractant of the Bark Beetle Pityophthorus pityographus
Author(s) -
Mori Kenji,
Puapoomchareon Prapai
Publication year - 1987
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.198719870321
Subject(s) - enantiomer , chemistry , thallium , stereochemistry , pheromone , medicinal chemistry , organic chemistry , botany , biology
Enantiomerically pure ( R )‐sulcatol ( 2a ) was synthesized from ethyl ( R )‐3‐hydroxybutanoate ( 3 ). Cyclization of ( R )‐ 2a with thallium(III) triacetate yielded (2 S ,5 R )‐pityol ( 1 ). In the same manner, ( S )‐ 2a and (2 R ,5 S )‐ 1 were synthesized from ( S )‐ 3 .