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

Sandrine Caix-Haumesser (1) , Issam Hanna (1) , Jean-Yves Lallemand (1) , Jean-François Peyronel (2)

1 DCSO - Laboratoire de synthèse organique
2 Aventis Pharma

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.

Sandrine Caix-Haumesser, Issam Hanna, Jean-Yves Lallemand, Jean-François Peyronel. Solid-phase synthesis of functionalized tropane derivatives via 1,3-dipolar cycloaddition. Tetrahedron Letters, 2001, 42 (22), pp.3721-3723. ⟨10.1016/s0040-4039(01)00565-2⟩. ⟨hal-00954879⟩