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Enantiospecific synthesis of (R)-1,7-dioxaspiro [5.5]undecane [major component of olive fruit fly (Dacus Oleae) sex
I I Cubero1, M T Plaza López-Espinosa, R A Castillo
1Department of Organic Chemistry, Faculty of Pharmacy, University of Granada, 18071, Granada, Spain.
Abstract:
The synthesis of the title compound13 has been carried out through the preparation of its precursor, (3R,4R,5S,6R)-3,4,5-trihydroxy-1,7-dioxaspiro[5.5]undecane (6), obtained fromD-fructose using Wittig's methodology, reduction, and spiroketalation. Compound6 was transformed into13 by a Barton deoxygenation at C-5 followed by a Corey dideoxygenation at C-3,4 of the appropriately protected derivatives.
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