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Free-radical Cyclization of Petroselinic Acid

✍ Scribed by Metzger, Jürgen O. ;Mahler, Ralf

Publisher
John Wiley and Sons
Year
1993
Tongue
English
Weight
299 KB
Volume
1993
Category
Article
ISSN
0947-3440

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✦ Synopsis

Abstract

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 SnCl~2~/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.

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