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Pheromone Syntheses, LXXVIII. Synthesis of the Four Thermodynamically Stable Stereoisomers of 2,7‐Dimethyl‐1,6‐dioxaspiro[4.6]undecane, a Component of the Volatile Secretion from the Mandibular Glands of Andrena haemorrhoa F.
Author(s) -
Mori Kenji,
Soga Hiroshi,
Ikunaka Masaya
Publication year - 1985
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.198519851109
Subject(s) - undecane , chemistry , enantiomer , pheromone , acetal , chirality (physics) , stereochemistry , component (thermodynamics) , botany , chiral symmetry breaking , quantum mechanics , nambu–jona lasinio model , biology , quark , thermodynamics , physics
The title compounds (2 R ,5 S ,7 R )‐ 1 , (2 S ,5 S ,7 R )‐ 1 , (2 R ,5 R ,7 S )‐ 1 , and (2 S ,5 R ,7 S )‐ 1 were synthesized from ethyl ( S )‐lactate ( 3 ) and the ( R )‐ or ( S )‐enantiomers of ethyl 3‐hydroxybutanoate ( 4a ). The formation of the spiro acetal 1 from 2b proceeds stereoselectively. Various spiro acetals with axial S ‐chirality at the spiro center were shown to be dextrorotatory at 589 nm.