Access to 3-Prenylated Oxindoles by α-Regioselective Prenylation: Application to the Synthesis of (±)-Debromoflustramine E.

ABSTRACT

The development of a rapid, highly efficient, and one-pot synthesis of C3-α-prenylated oxindoles with simple reagents is described. The process is based on zinc-mediated α-regioselective prenylation of 3-acylidene-oxindole with commercially available prenyl bromide using inexpensive CeCl3 as the catalyst. The new transformation tolerates a wide range of 3-acylidene-oxindoles, providing easy access to a variety of functionalized 3-prenylated oxindoles. The synthetic utility of the approach is verified by formal synthesis of the flustramine family alkaloid (±)-debromoflustramine E.