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Pheromone Synthesis, LXIV. Synthesis of the Enantiomers of 2‐Methyl‐1,7‐dioxaspiro[5.6]‐dodecane, a Component of the Volatile Secretion from the Mandibular Glands of Andrena haemorrhoa F.
Author(s) -
Mori Kenji,
Katsurada Manabu
Publication year - 1984
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.198419840116
Subject(s) - enantiomer , pheromone , sex pheromone , dodecane , chemistry , stereochemistry , secretion , biology , botany , organic chemistry , biochemistry
The syntheses of the title compounds (2 R ,6 S )‐ 1 and (2 S ,6 R )‐ 1 from ( R )‐ and (S)‐β‐hydroxybutyrate 3 are described. The formation of the spiroacetal 1 from ( R )‐ 9 proceeded stereoselectively to give only (2 R ,6 S )‐ 1 . Similarly ( S )‐ 9 yielded (2 S ,6 R )‐ 1 .