US scientists have made multifunctional lactones – normally a challenging process – in an efficient way, under mild conditions and without protecting groups or by-products.
Multifunctional molecules are attractive for cellular targeting, imaging and drug delivery or as synthetic mimics of biological structure and function.
The team began with a symmetrical trifunctional molecule – benzotrifuranone – and sequentially functionalised its three reactive sites by aminolysis. The functional groups were designed in such a way that each functionalisation diminishes the reactivity of the remaining sites so that the groups only functionalise one reactive site each time.
Reference:
Molecular multifunctionalization via electronically coupled lactones
M B Baker, I Ghiviriga and R K Castellano, Chem. Sci., 2012
DOI: 10.1039/c2sc00943a
