Enantiospecific synthesis fromd-fructose of (2S,5R)- and (2R,5R)-2-methyl-1,6-dioxaspiro[4.5]decane [the odor bouquet minor components ofParavespula vulgaris (L.)] |
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| Authors: | Isidoro Izquierdo Cubero Maria T. Plaza Lopez-Espinosa Anthony C. Richardson |
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| Affiliation: | (1) Department of Organic Chemistry, Faculty of Pharmacy, University of Granada, 18071 Granada, Spain;(2) Department of Chemistry, King's College London, University of London Strand, WC2R 2LS London, UK |
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| Abstract: | 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 fromd-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.Enantiospecific synthesis of spirocetals. Part V. For Part IV, see Izquierdo et al. (1992). |
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| Keywords: | Enantiospecific synthesis spiroacetal font-variant:small-caps" >d-fructose pheromone Paravespula vulgaris |
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