The first stereoselective synthesis of the natural product, rotenone

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• 作者：Kathy Hadje Georgiou ; Stephen C. Pelly¹ ; Charles B. de Koning ; ^{Charles.deKoning@wits.ac.za}
• 关键词：Rotenoid ; Rotenone ; Munduserone ; Dihydrobenzofuran ; 6-Endo-hydroarylation ; Chromene ; Total synthesis
• 刊名：Tetrahedron
• 出版年：2017
• 出版时间：16 February 2017
• 年：2017
• 卷：73
• 期：7
• 页码：853-858
• 全文大小：643 K
• 卷排序：73

文摘

The total syntheses of rotenone and munduserone are reported in this paper. The synthesis of rotenone involves two key transformations, the first of which is a Pd π-allyl mediated cyclisation for the construction of the dihydrobenzofuran skeleton. The second is a 6-endo-hydroarylation which yields the chromene as a precursor to rotenone. The synthesis of rotenone was achieved in 17 steps from resorcinol and constitutes the first stereoselective synthesis of this complex natural product.