Solid-phase synthesis of functionalized tropane derivatives via 1,3-dipolar cycloaddition

Abstract : 1,3-Dipolar cycloaddition of 3-oxidopyridinium betaine to activated olefins on solid-phase leads to resin-bound 8-azabicyclo[3.2.1]octenones which undergo further transformations such as 1,4-addition of nucleophiles. Cleavage of benzyl linker is achieved using acid chlorides in the presence of potassium iodide to give substituted tropane derivatives. © 2001 Elsevier Science Ltd.