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Enantioselective synthesis of dolabelide c.

Abstract : Few specific studies have previously been spent building diol-1, 3 syn functionalized α by a double bond. In contrast, the synthesis of triols-1, 3,5 have been many subsequent publications, it appeared Interestingly, before stating our results, to devote the first part methods existing in the literature for the diastereoselective synthesis of these polyols. We then present our general strategy to develop these two types of structures. It involves a common precursor easily accessible, the vinylsulfone I and is shown in the diagram below retrosynthetic cons. Our approach to developing 1,3,5 triols based on Julia coupling type between β-Hydroxy II - so diastereoselective obtained from I - and a carbonyl compound. This approach will be developed during a second part. The third part will be devoted to the construction of 1.3-diols syn functionalized in α by a double bond. These could be obtained after a coupling of I carbonyl compound leading to intermediate IV, by adding a sequence combination / elimination, followed by a reduction of vinyl sulfone. A final section will be devoted to the development of a new method deprotection of ethers triéthylsilyle highlighted in our work.
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Delphine Rotulo-Sims. Enantioselective synthesis of dolabelide c.. Chemical Sciences. Ecole Polytechnique X, 2005. English. ⟨pastel-00001438⟩

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