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

Abstract

AbstractA 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.magnified image