Page 15 - Volume 3, Issue 2, July 2010

© Benaki Phytopathological Institute
Mosquito oviposition aggregation pheromone 45
They also developed ZrCl 4-catalyzed depro-
tection of 1,3-dioxane and ring closure to
prepare a benzyloxy-substituted tetrahy-
dropyrane as the key intermediate (7 steps,
28% yield ).
Methyl trans- hexa-5-decenoate was di-
hydroxylated by Lohray and Venkateswar-
lu, (1997) using Sharpless asymmetric dihy-
droxylation reaction followed by treatment
with thionyl chloride to furnish cyclic sulfite
as the major product (Figure 21). The cyclic
sulfite was oxidized to the cyclic sulfate. The
methyl ester of cyclic sulfate 36 was hydro-
lysed to affect an intramolecular cyclization
by the in situ generated carboxylate ion with
concomitant SN2 intramolecular ring open-
ing of cyclic sulfate with inversion of config-
uration at the reacting center. Acetylation
Figure 20
Figure 21
Figure 19