Methyl undecylenate reduction

The sex pheromone structure, 10-methyl-2-tridecanone, was synthesized using the carboxyl group as the source of the methyl branch (lA) (Figure 6). Undecylenic acid was a-propylated and resolved via amides. The procedure followed allowed us to obtain the alcohols,(R)- and (S)-2-propyl-10-undecenol (>99.6% ee). The corresponding bromide was reduced with lithium triethylborohydride (15) then the double bond was converted to a methyl ketone by a) oxymercuration, b) reduction of the C-Hg bond with sodium borohy-dride, and c) oxidation with dichromate. The male southern corn rootworm responds only to the (R)-configuration no biological activity was noted for the (S)-enantiomer. Therefore, in this instance the racemic compound would be predicted to monitor this species adequately. 

---

See also in sourсe #XX -- [ ]

See also in sourсe #XX -- [ ]

See also in sourсe #XX -- [ ]

---