Taming of a Superbase for Selective Phenol Desilylation and Natural Product Isolation
                                
                                    
                                        作者:Darci J. Trader、Erin E. Carlson                                    
                                    
                                        DOI:10.1021/jo4010298
                                    
                                    
                                        日期:2013.7.19
                                    
                                    Hydroxyl moieties are highly prevalent in natural products. We previously reported a chemoselective strategy for enrichment of hydroxyl-functionalized molecules by formation of a silyl ether bond to a resin. To generate smaller pools of molecules for analysis, we developed cleavage conditions to promote stepwise release of phenolic silyl ethers followed by aliphatic silyl ethers with a "tamed" version of the superbase 1,1,3,3-tetramethylguanadine. We demonstrate this as a general strategy for selective deprotection of phenolic silyl ethers under neutral conditions at room temperature.