title: Enantiospecific synthesis of (R)-1,7-dioxaspiro [5.5]undecane [major component of olive fruit fly (Dacus Oleae) sex pheromone] from d-Fructose.
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.
authors.affiliation: Department of Organic Chemistry, Faculty of Pharmacy, University of Granada, 18071, Granada, Spain.
authors.forename: I I
authors.initials: II
authors.lastname: Cubero
authors.forename: M T
authors.initials: MT
authors.lastname: Plaza López-Espinosa
authors.forename: R A
authors.initials: RA
authors.lastname: Castillo