ISSN:
0170-2041
Keywords:
(±)-Phoracantholide, monofluorinated
;
Lactones
;
Fatty acids
;
Epoxides
;
Fluorohydrines
;
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
10-Fluorodecan-9-olide (1a), a monofluorinated analogue of (±)-phoracantholide, is synthesised in 20% overall yield by a five-step sequence starting with 9-decenoic acid (3a). 10-Undecenoic acid (3b) is transformed in 28% overall yield into the next higher homologue, 11-fluoroundecan-10-olide (1b). Their regioisomers, 9-fluorodecan-10-olide (2a) and 10-fluoroundecan-11-olide (2b), are obtained analogously in 20% or 29% yield. Key step of these syntheses is the regioselective opening of the epoxides of unsaturated fatty acid esters 5a and 5b.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/jlac.199419940913
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