The 4-methoxybenzyl (MPM) protectinggroup for hydroxy functions is readily removed with DDQ in dichloromethane containing a small amount of water at room temperature. Under these neutral conditions, several other protecting and functional groups remained unchanged. 3,4-Dimethoxybenzyl (DMPM) groups are more reactive than MPM groups with DDQ. The benzyl (Bn) protectinggroup was removed by catalytic
Synthesis of Frame-Shifted Farnesyl Diphosphate Analogs
作者:Andrew T. Placzek、James L. Hougland、Richard A. Gibbs
DOI:10.1021/ol300683r
日期:2012.8.17
A set of synthetic approaches were developed and applied to the synthesis of eight frame-shifted farnesyl diphosphate (FPP) analogs. These analogs bear increased or decreased methylene units between the double bonds and/or diphosphate moieties of the isoprenoid structure. Evaluation versus mammalian FTase revealed that small structural changes can lead to dramatic changes in substrate ability.