Synthesis of Chiral, Fused Tricyclic Molecules by Sequential Metal-Catalyzed Reactions of Simple Substrates

Identifier:  imarina:9283531

Handle: https://hdl.handle.net/20.500.11797/imarina9283531

Authors:  Saltó, J; Biosca, M; Pàmies, O; Diéguez, M

Abstract:
A set of complex tricyclic compounds containing several functional groups and multiple stereogenic centers has been prepared in only two steps with excellent diastereo- and enantioselectivities. The synthesis takes advantage of the highly versatile and enantioselective Pd-catalyzed allylic substitution of simple cyclic allylic acetates or carbonates to form chiral 1,6-, 1,7- and 1,8-enynes, which are then diastereoselectively transformed to the corresponding cyclopentenone- and cyclobutene-based tricyclic compounds.