ORGN 549 |
| Spiroacetals are widespread substructures of biologically active natural products. While most 6,6 spiroacetals adopt a conformation corresponding to double anomeric stabilization, in certain stereochemical arrangements found in some natural products the conformation adopted lacks stabilization by the anomeric effect. The (2S,6S,8S)-2,8-dimethyl-1,7-dioxaspiro-[5.5]-undecane pheromonal secretions of the cucumber fly Dacus cucumis are illustrative of this phenomenon. Organometallic chirons such as 1 may be uniquely qualified for the construction of contrathermodynamic spiroacetals because the spiroacetal linkage and substituent absolute stereochemistries can be fully controlled by the metal moiety. Recent effort toward the synthesis of the non-anomeric spiroacetal 3 using a hetero Diels-Alder cycloaddition as the key step will be discussed.
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Heterocycles, Aromatics, Metal-Mediated Reactions and Syntheses, Materials, Devices, and Switches
8:00 PM-10:00 PM, Wednesday, 29 March 2006 Georgia World Congress Center -- Ex. Hall B4, Poster
Division of Organic Chemistry |
