Enantiospecific synthesis of (R)-1,7-dioxaspiro [5.5]undecane [major component of olive fruit fly (Dacus oleae) sex pheromone] from D-fructose
1991
Izquierdo Cubero, I. | Plaza Lopez-Espinosa, M.T. | Acuna Castillo, R.
The synthesis of the title compound 13 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 from D-fructose using Wittig's methodology, reduction, and spiroketalation. Compound 6 was transformed into 13 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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