Lux Michaelyn C, Boby Melissa L, Brooks Joshua L, Tan Derek S
Tri-Institutional PhD Program in Chemical Biology, Memorial Sloan Kettering Cancer Center, 1275 York Avenue, New York, New York 10065, USA.
Pharmacology Program, Weill Cornell Graduate School of Medical Sciences, Memorial Sloan Kettering Cancer Center, 1275 York Avenue, New York, New York 10065, USA.
Chem Commun (Camb). 2019 Jun 21;55(49):7013-7016. doi: 10.1039/c9cc03775f. Epub 2019 May 31.
Bicyclic ether scaffolds are found in a variety of natural products and are of interest in probe and drug discovery. A palladium-catalyzed cascade reaction has been developed to provide efficient access to these scaffolds from readily available linear diene-diol substrates. A Pd redox-relay process is used strategically to transmit reactivity between an initial oxypalladative cyclization and a subsequent π-allyl-Pd cyclization at remote sites. The reaction affords a variety of bicyclic ether scaffolds with complete diastereoselectivity for cis-ring fusion.
双环醚骨架存在于多种天然产物中，在探针和药物发现方面具有重要意义。已开发出一种钯催化的串联反应，可从容易获得的线性二烯二醇底物高效合成这些骨架。战略性地使用钯氧化还原中继过程，以在初始氧钯化环化和远程位点随后的π-烯丙基钯环化之间传递反应性。该反应以完全的非对映选择性提供了各种双环醚骨架，用于顺式环稠合。
