Protecting-Group-Free Total Synthesis of (鈭?-Jiadifenolide: Development of a [4 + 1] Annulation toward Multisubstituted Tetrahydrofurans

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• 作者：Yang Shen ; Linbin Li ; Zhisheng Pan ; Yinglu Wang ; Jundong Li ; Kuangyu Wang ; Xiance Wang ; Youyu Zhang ; Tianhui Hu ; Yandong Zhang
• 刊名：Organic Letters
• 出版年：2015
• 出版时间：November 6, 2015
• 年：2015
• 卷：17
• 期：21
• 页码：5480-5483
• 全文大小：411K
• ISSN：1523-7052

文摘

A concise, protecting-group-free total synthesis of (鈭?-jiadifenolide, a synthetically challenging seco-prezizaane sesquiterpene with potent neurotrophic activity, is reported. The convergent route features a SmI₂/H₂O-mediated stereoselective reductive cyclization, an unprecedented formal [4 + 1] annulative tetrahydrofuran-forming reaction and programmed redox manipulations. The newly developed annulation of 尾-hydroxy aldehydes or ketones with lithium trimethylsilyldiazomethane provides access to a diverse array of multisubstituted tetrahydrofurans. The synthetic jiadifenolide exhibited weak cytotoxicity against five human cancer cell lines.