Synthesis of SL0101 Carbasugar Analogues: Carbasugars via Pd-Catalyzed Cyclitolization and Post-Cyclitolization Transformations

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• 作者：Mingde Shan ; George A. O’ ; Doherty
• 刊名：Organic Letters
• 出版年：2010
• 出版时间：July 2, 2010
• 年：2010
• 卷：12
• 期：13
• 页码：2986-2989
• 全文大小：278K
• 年卷期：v.12,no.13(July 2, 2010)
• ISSN：1523-7052

文摘

A general approach to the stereoselective synthesis of 5a-carbasugars has been developed. The route mimics our palladium-catalyzed glycosylation/postglycosylation approach to carbohydrates in that it also utilizes a highly regio- and stereospecific palladium-catalyzed allylation and postglycosylation reaction sequence for the installation of either an class="smallcaps">dan>- or an class="smallcaps">lan>-cyclitols. This cyclitolization/postcyclitolization sequence was used for the enantioselective synthesis of a cyclitol analogue of SL0101, its an class="smallcaps">dan>-sugar enantiomer, as well as several acetylation pattern analogues.