Tandem C–H oxidation/cyclization/rearrangement and its application to asymmetric syntheses of (−)-brussonol and (−)-przewalskine E

• Published in: Nature communications 2015-06, Vol.6 (1), p.7332-7332, Article 7332
• Main Authors: Jiao, Zhi-Wei, Tu, Yong-Qiang, Zhang, Qing, Liu, Wen-Xing, Zhang, Shu-Yu, Wang, Shao-Hua, Zhang, Fu-Min, Jiang, Sen
• Format: Article
• Language: English
• Subjects: 140/131; 639/638/403/349; 639/638/403/937; 639/638/77/889; Benzoquinones - chemistry; Diterpenes - chemical synthesis; Humanities and Social Sciences; Indium - chemistry; multidisciplinary; Science; Science (multidisciplinary)
• ISSN: 2041-1723; 2041-1723
• DOI: 10.1038/ncomms8332

Natural products are a vital source of lead compounds in drug discovery. Development of efficient tandem reactions to build useful compounds and apply them to the synthesis of natural products is not only a significant challenge but also an important goal for chemists. Here we describe a tandem C–H oxidation/cyclization/rearrangement of isochroman-derived allylic silylethers, promoted by DDQ and InCl 3 . This method allows the efficient construction of tricyclic benzoxa[3.2.1]octanes with a wide substrate scope. We employ this tandem reaction to achieve the asymmetric total syntheses of (−)-brussonol and (−)-przewalskine E . The ability to form complex molecular architectures from simpler precursors is important for drug discovery and medicinal chemistry. Here, the authors report a cascade reaction giving access to tricyclic products and apply it in the total synthesis of two natural products.