Preparation of novel 2-(trialkylsilyl)ethyl linkers and first synthesis of Tryprostatin B on solid phase

Two synthetic methods for novel polymer-supported 2-(trialkylsilyl)ethanol linkers 3 are described. The new silyl linker has been examined as a C-terminal linkage to provide several diketopiperazines. Using this synthetic method, the first solid phase synthesis of Tryprostatin B was accomplished. Several functionalized 2-(trialkylsilyl)ethyl linkers 12–17 are synthesized from 2-(trialkylsilyl)ethanol linkers. During the course of preparations, the new silyl linkers proved resistant to various reaction conditions such as basic and moderately acidic media, oxidation, and elevated thermal conditions.