Methylation of the beta-positions of the furan ring in F-acids.
Major incubation products in feeding experiments with the sodium salt of 7-(5-butyl-furan-2-yl)heptanoic acid (3) on suspension cultures of Saccharum spec. are the unusual F-acids (4a) and (4b). They possess in contrast to natural monomethyl substituted F-acids a methyl substituent in the 4-position of the furan ring. Unexpectedly, the dimethyl substituted F-acids (4c) and (4d) were found only in very small amounts. The detection and structure elucidation of the methylation products (4a)-(4d) was achieved predominantly by GC-MS analysis of the corresponding tetrahydrofuran derivatives (5a)-(5d).
Scheinkönig
J
J
Lehrstuhl Organische Chemie I, Universität Bayreuth, Germany.
Hannemann
K
K
Spiteller
G
G
D002478:Cells, Cultured; D005227:Fatty Acids / Q000737:chemistry*; D005663:Furans / Q000737:chemistry*; D008401:Gas Chromatography-Mass Spectrometry; D008745:Methylation; D010944:Plants / Q000737:chemistry*
D005227:Fatty Acids; D005663:Furans