A Highly Convergent Total Synthesis of Leustroducsin B

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• 作者：Barry M. Trost ; Berenger Biannic ; Cheyenne S. Brindle ; B. Michael O鈥橩eefe ; Thomas J. Hunter ; Ming-Yu Ngai
• 刊名：Journal of the American Chemical Society
• 出版年：2015
• 出版时间：September 16, 2015
• 年：2015
• 卷：137
• 期：36
• 页码：11594-11597
• 全文大小：356K
• ISSN：1520-5126

文摘

Leustroducsin B exhibits a large variety of biological activities and unique structural features. An efficient and highly convergent total synthesis of Leustroducsin B was achieved in 17 longest linear and 39 total steps by disconnecting the molecule into three fragments having similar levels of complexity. These pieces were connected via a highly efficient chelate-controlled addition of a vinyl zincate to an 伪-hydroxy ketone and a silicon-mediated cross-coupling. The stereochemistry of the central and western fragments was set catalytically in high yields and excellent de by a zinc-ProPhenol-catalyzed aldol reaction and a palladium-catalyzed asymmetric allylic alkylation.