The objective of this research is to synthesize novel phospholipids to be used in exogenous lung surfactant preparations for the treatment of acute respiratory distress syndrome (ARDS). The lipids are intended to be resistant to lipase degradation, while maintaining the exceptional surface activity of their natural counterparts. Accordingly, diether phosphonolipid analogues of DPPC (dipalmitoyl phosphatidylcholine) and DPPG (dipalmitoyl phosphatidylglycerol) were targeted. Additionally, an unsaturated lipid was prepared, also bearing the 3,4-dihydroxybutyl hydrogen phosphonate headgroup. Not only are these latter compounds novel, but they represent the first of a new class of phosphonoglycerol lipid. However, the methods used to obtain the phosphonolipids involve low yielding reactions and suffer from other cost and labour inefficiencies. Hoping to economize production, alternative synthetic routes were devised and investigated.