利用铟介导的Reformatsky-Claisen重排反应全合成(-)-二氢孢子内酯
Total synthesis of (-)-dihydrosporothriolide utilizing an indium-mediated Reformatsky-Claisen rearrangement.
作者信息
Ishihara Jun, Tsuru Hiroaki, Hatakeyama Susumi
机构信息
Graduate School of Biomedical Sciences, Nagasaki University , 1-14 Bunkyo-machi, Nagasaki 852-8521, Japan.
出版信息
J Org Chem. 2014 Jun 20;79(12):5908-13. doi: 10.1021/jo5008948. Epub 2014 Jun 11.
The asymmetric synthesis of (-)-dihydrosporothriolide (1), a biologically active bis-γ-butyrolactone, is described, that proceeds through a D-proline-catalyzed asymmetric aminooxylation, indium-mediated Reformatsky-Claisen rearrangement of an α,α-dibromoacetate derivative, and diastereoselective dihydroxylation. The route requires no protective group manipulation and allows the concise seven-step synthesis of 1 from n-octanal.
描述了生物活性双γ-丁内酯（-）-二氢孢子内酯（1）的不对称合成，该合成过程通过D-脯氨酸催化的不对称氨氧基化、铟介导的α，α-二溴乙酸酯衍生物的Reformatsky-Claisen重排以及非对映选择性二羟基化反应进行。该路线无需进行保护基操作，并且能够从正辛醛出发，经简洁的七步反应合成1。
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