ISSN:
0170-2041
Keywords:
Apis mellifica L
;
Pheromones
;
Alkynols
;
2-Decenoic acid, (E)-9-hydroxy
;
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Simple Synthesis of the Enantiomeric (E)-9-Hydroxy-2-decenoic AcidsThe enantiomeric (E)-9-Hydroxy-2-decenoic acids (1), components of the swarm settling pheromone in Apis mellifica L. (honey bee) have been synthesized. The lithium derivative of 1-hexyne was treated with (R)-(+)-methyloxirane (2), (S)-(-)-2 or (±)-2 to give the alkynols (R)-(-)-3, (S)-(+)-3 or (±)-3, which could be isomerized with the sodium salt of 1,3-propanediamine to give (R)-(-)-8-nonyn-2-ol (4) and (±)-4. These were methoxycarbonylated to produce the esters (R)-(-)-5, (S)-(+)-5 or (±)-5. Selective hydrogenation in pyridine with Pd/BaSO4 as catalyst gave the (Z)-esters (R)-(-)-6, (S)-(+)-6 or (±)-6 which could be isomerized with photochemically generated phenylthio radicals to produce the (E)-esters (R)-(-)-7, (S)-(+)-7 or (±)-7. The acids present in the pheromone (R)-(-)-1, (S)-(+)-1 and (±)-1 could be obtained by basic hydrolysis of the esters. The minor but important component 8 of the swarm settling pheromone has been synthesized by treating the Grignard reagent obtained from 5-bromo-guaiacol benzyl ether with ethylene oxide to give 9 in high yield. Hydrogenolytic removal of the benzyl group in 9 produced 8 directly.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/jlac.199419940213
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