Versatile Configuration-Encoded Strategy for Rapid Synthesis of 1,5-Polyol Stereoisomers

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• 作者：Gregory K. Friestad ; Gopeekrishnan Sreenilayam
• 刊名：Organic Letters
• 出版年：2010
• 出版时间：November 5, 2010
• 年：2010
• 卷：12
• 期：21
• 页码：5016-5019
• 全文大小：241K
• 年卷期：v.12,no.21(November 5, 2010)
• ISSN：1523-7052

文摘

The isolated stereogenic centers of 1,5-polyol-containing natural products present challenges to synthesis and structure determination. To address this problem, a configuration-encoded strategy defines each configuration within a simple 4-(arylsulfonyl)butyronitrile building block, a repeat unit that is reliably and efficiently coupled in iterative fashion to afford 1,5-polyols of defined stereochemistry. For example, the C27−C40 subunit of tetrafibricin is prepared in five steps and 42% yield. This strategy is amenable to rapid and unambiguous preparation of all configurational permutations of 1,5-polyols with equal facility.