Abstract
(2R,4R,6R,8R)-2,4,6,8-Tetramethyldecanoic- and -undecanoic Acid of the Preen-gland Wax from the Domestic Goose, Anser a.f. domesticus: Isolation, Synthesis of Derivatives and of the rac-2,4,6,8-Tetramethyldecanoic Acid Large quantities of (2R,4R,6R,8R)-2,4,6,8-tetramethyldecanoic- and -undecanoic acid methyl ester (3 and 4) were obtained after transesterification and Spaltrohr® distillation of the preen-gland wax of the domestic goose. Hydrolysis with NaOH/dioxan afforded the acids 5 and 6. Reduction of 3 with LiAlH4 gave (2R,4R,6R,8R)-2,4,6,8-tetramethyldecanol (7). Esterification of 5 and 6 with octadecanol yielded the pure wax esters 1 and 2, while 5 with glycerol gave the triglyceride 9 and 5 with 7 afforded 8. Alcohol 7 and octadecyl bromide, in the presence of NaH/DMF, afforded the ether 10. The racemic acid 22, corresponding to 5, was obtained synthetically by starting with a modified Wittig reaction of 2-(diethoxyphosphoryl)propionic acid ethyl ester on 2-methylbutyraldehyde. Transesterification of the ethyl ester 21 with octadecanol gave the racemic wax ester 23, corresponding to 1. The optical activity and 13C data of the compounds are reported.
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