ISSN:
0947-3440
Keywords:
5,6-Dihydroxyhexadecanoic acid derivatives
;
δ-Lactones
;
Resolution, kinetic
;
Lipases
;
Mosquito pheromone
;
Pheromones
;
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
The methyl ester rac-4a of (5R*,6S*)-5,6-dihydroxyhexadecanoic acid was prepared by a Wittig reaction of (4-carboxybutyl)triphenylphosphonium bromide (2) with undecanal (1) followed by esterification with methanol and cis dihydroxylation with osmium (VIII) oxide/N-methylmorpholine N-oxide. After conversion of the dihydroxy ester rac-4a into (5R*,6S*)-6-hydroxyhexadecan-5-olide (rac-5) by lactonization (5R,6S)-6-acetoxyhexadecan-5-olide (6), the mosquito oviposition attractant pheromone, was obtained by an enantioselective lipase-catalyzed acetylation with vinyl acetate. In an alternative route the dihydroxy ester rac-4a was subjected to a lipase-catalyzed lactonization, which afforded as the main product (5S,6R)-6-hydroxyhexadecan-5-olide (ent-5), the enantiomer of the deacetylated pheromone.
Additional Material:
1 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/jlac.1995199505132
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