ISSN:
0170-2041
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Description / Table of Contents:
Asymmetric Synthesis of Both Enantiomers of (E)-4,6-Dimethyl-6-octen-3-one- Defensive Substance of “Daddy Longlegs” Leiobunum vittatum and L. calcar (Opiliones)The acyclic enone (E)-4,6-dimethyl-6-octen-3-one (1) is the major component of the defensive secretion of “daddy longlegs” Leiobunum vittatum and L. calcar (Opiliones). Both antiomers [(S)-1 and (R)-1] as well as racemic 1 are conveniently synthesized from diethyl ketone 2 and the bromide 3 by employing the hydrazone method. It is shown by LIS-NMR technique that the acyclic ketone alkylation occurs with virtually complete asymmetric induction ≥ 97%).
Notes:
Das acyclische Enon (E)-4,6-Dimethyl-6-octen-3-on (1) ist die Hauptkomponente Abwehrsekrets der Weberknechte Leiobunum vittatum und L. calcar (Opiliones). Beide Enantiomere [(S)-1 und (R)-1] sowie racemisches 1 werden bequem aus Diethylketon 2 und dem Bromid 3 unter Verwendung der Hydrazon-Methode synthetisiert. Durch LIS-NMR-Technik gezeigt, daß die acyclische Ketonalkylierung mit praktisch vollständiger asymmetrische? On erfolgt (ee ≥ 97%).
Additional Material:
1 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/jlac.198319830816
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