Enantiospecific synthesis from D-fructose of (2S,5R)- and (2R,5R)-2-methyl-1,6-dioxaspi-RO[4.5]decane [the odor bouquet minor components of Paravespula vulgaris (L.)].
1993
Izquierdo Cubero I. | Lopez Espinosa M.T.P. | Richardson A.C.
The synthesis of (2S,5R)- (1) and (2R,5R)-2-methyl-1,6-dioxaspiro[4.5]decane (2) from (2RS,5R,8R,9R,10S)-8,9,10-trihydroxy-2-methyl-1,6 dioxaspiro[4.5]decane (8), obtained in five steps from D-fructose using Wittig's methodology, reduction, and spiroketalation, has been accomplished by a Corey dideoxygenation at C-8,9, followed by a Barton deoxygenation at C-10, of the appropriately protected derivatives.
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