Synthesis of a tricyclic ketal: Possible attractant of Aedes aegypti
by Dutter, Brendan F., M.S., STATE UNIVERSITY OF NEW YORK COL. OF ENVIRONMENTAL SCIENCE & FORESTRY, 2009, 122 pages; 1482099

Abstract:

The tricyclic ketal 2,2,6,8-tetramethyl-7,11-dioxatricyclo[6.2.1.0 1,6]undecane was isolated from fermenting oak leaves and may be an oviposition attractant of Aedes aegypti, the principal vector of dengue fever. In order to confirm the structure, determine which of the two possible diastereomers is active, and provide enough material for further bioassays, syntheses of both molecules were undertaken with the goal of obtaining a keto-diol precursor and subjecting this to acidic conditions to induce ketalization. A trans keto-diol was obtained by epoxidizing the tetrasubstituted double bond of β-ionone followed by acid catalyzed hydrolysis. Attempts to form a ketal with the trans configuration were not successful and side products were observed. Synthesis of the cis isomer involved introducing an allylic alcohol onto α-ionone followed by a directed syn-epoxidation and epoxide opening to give the desired stereochemistry. This keto-diol formed the desired ketal under mildly acidic conditions. The cis-ketal matches the spectral data of the isolated compound.

Keywords: Tricyclic ketal, 2,2,6,8-tetramethyl-7,11-dioxatricyclo[6.2.1.0 1,6]undecane, Aedes aegypti, oviposition attractant, β-ionone, α-ionone, directed epoxidation

 
AdviserFrancis X. Webster
SchoolSTATE UNIVERSITY OF NEW YORK COL. OF ENVIRONMENTAL SCIENCE & FORESTRY
SourceMAI/ 49-02, p. , Oct 2010
Source TypeThesis
SubjectsOrganic chemistry
Publication Number1482099
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