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Free‐radical Cyclization of Petroselinic Acid
Author(s) -
Metzger Jürgen O.,
Mahler Ralf
Publication year - 1993
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.199319930136
Subject(s) - tributyltin hydride , chemistry , yield (engineering) , stereoselectivity , bicyclic molecule , hydride , tributyltin , medicinal chemistry , organic chemistry , hydrogen , materials science , metallurgy , catalysis
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.