ISSN:
0170-2041
Keywords:
Radicals
;
Cyclizations, intramolecular
;
Petroselinic acid
;
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Petroselinic acid was cyclized via methyl 2-iodopetroselinate (1) with tributyltin hydride to give methyl trans- and cis-2-dodecyl-1-cyclopentanecarboxylate (2). The atom-transfer method with hexabutylditin resulted in the formation of bicyclic γ-lactones 4 and methyl trans-2-(1′-iodododecyl)-1-cyclopentanecarboxylate (trans-5). The same products were obtained with the new initiator system SnCl2/AgOAc. This method showed, if compared with the other methods, the shortest reaction time, the highest yield and stereoselectivity combined with a very simple workup procedure and the use of less toxic chemicals.
Additional Material:
1 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/jlac.199319930136
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