[4 + 2]-Annulations of Chiral Organosilanes: Application to the Total Synthesis of Leucascandrolide A

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• 作者：Qibin Su ; Les A. Dakin ; James S. Panek
• 刊名：Journal of Organic Chemistry
• 出版年：2007
• 出版时间：January 5, 2007
• 年：2007
• 卷：72
• 期：1
• 页码：2 - 24
• 全文大小：578K
• 年卷期：v.72,no.1(January 5, 2007)
• ISSN：1520-6904

文摘

Complete details of an asymmetric synthesis of leucascandrolide A (1) are described. The synthesishighlights the use of two diastereoselective [4 + 2]-annulations for the assembly of the functionalizedbispyranyl macrolide 3. An efficient assembly and union of the oxazole-containing side chain 4 withmacrolide 3 was carried out using a Mitsunobu reaction. A convergent route to the oxazole side chainwas developed using a Sonogashira cross-coupling between 2-trifloyloxazole 16 and alkyne 17, whichallowed for the installation of the C9'-C10' (Z)-olefin.