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Nouveaux spiroacétals incorporant des hétéroatomes en bêta du carbone spiranique : synthèse et études structurales

Abstract : The spiroketal moiety forms a part of the skeleton of many natural products that present various biological activities. Recently, new synthetic spiroketal compounds with a supplementary heteroatom in beta position from the spiranic carbon and with interesting biological activities, were reported. We developed an effective and modular synthesis of original spiroketals incorporating heteroatoms (oxygen, sulphur, nitrogen) at the 4 and 10 positions of 1,7- dioxaspiro[5.5]undecane framework. It is based on a deprotection-spirocyclization key step of a masked ketone obtained after nucleophilic substitution of the 1,3-dichloropropanone Obenzyloxime with precursors synthesized from solketal. That way, we prepared 4,10-dioxa-, 4,10-dithia-, 4-thia-10-oxa-, 10-aza-4-thia- and 10-aza-4-oxa-1,7-dioxaspiro[5.5]undécanes, for which a complete structural study was realized by NMR experiments. First exploring towards 4,10-diaza- moiety is also presented.
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https://theses.hal.science/tel-00717740
Contributor : Camille Meyer Connect in order to contact the contributor
Submitted on : Friday, July 13, 2012 - 3:07:54 PM
Last modification on : Tuesday, December 14, 2021 - 10:38:06 AM
Long-term archiving on: : Thursday, December 15, 2016 - 11:14:33 PM

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  • HAL Id : tel-00717740, version 1

Citation

Marlène Goubert. Nouveaux spiroacétals incorporant des hétéroatomes en bêta du carbone spiranique : synthèse et études structurales. Chimie analytique. Université Blaise Pascal - Clermont-Ferrand II, 2007. Français. ⟨NNT : 2007CLF21731⟩. ⟨tel-00717740⟩

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