Abstract
The synthesis of (3S,6R)-3-hydroxy-1,7-dioxaspiro[5.5]undecane (8) and its (4R)-4-hydroxy isomer (11) from (3R,4S,6R)-3,4-dihydroxy-1,7-dioxaspiro[5.5]undecane (1), obtained from D-fructose, has been accomplished by regioselective deoxygenation at C-4 and C-3, respectively, of the appropriately protected derivatives.
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Enantiospecific synthesis of spiroacetals. Part III. For Part II, see Izquierdo et al. (1991).
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Izquierdo Cubero, I., Plaza López-Espinosa, M.T. & Castillo, R.A. Enantiospecific synthesis of (3S,6R)-3-hydroxy-1,7-dioxaspiro[5.5]undecane and its (4R)-4-hydroxy isomer [minor components of olive fruit fly (Dacus oleae) sex pheromone]. J Chem Ecol 18, 115–125 (1992). https://doi.org/10.1007/BF00993747
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DOI: https://doi.org/10.1007/BF00993747