Synthese von optisch aktiven Trogoderma-Pheromonen durch Kolbe-Elektrolyse
The (R)-(-)-enantiomers of (Z)- (1) and (E)-14-methyl-8-hexadecen-1-ol (2) have been synthesized by coelectrolysis of (R)-(-)-4-methylhexanoic acid (7) with 12-(tetrahydro-2-pyranyloxy)-4-dodecynoic acid (8) and its subsequent hydrogenation.The acid 7 was prepared in high optical purity from (S)-(-)-citronellol (3) by conversion of the hydroxyl group to a methyl substituent and subsequent cleavage of (R)-(-)-2,6-dimethyl-2-octene (4) with ozone.By alkylation of 4-pentynoic acid (5) with 1-bromo-7-(tetrahydro-2-pyranyloxy)heptane (6) the alkynoic acid 8 was synthesized.
Jensen, Uta,Schaefer, Hans-J.
p. 292 - 297
(2007/10/02)
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