A new approach to alkaloid-like systems: synthesis and crystal structure of 1-(2-acetyl-11-meth-oxy-5,6-di-hydro-[1,3]dioxolo[4,5- g ]pyrrolo-[2,1- a ]isoquinolin-1-yl)propan-2-one.

The title compound, C19 H19 NO5 , (I), is the product of a domino reaction between cotarnine chloride and acetyl-acetylene catalysed by copper(I) iodide. The mol-ecule of (I) comprises a fused tetra-cyclic system containing two terminal five-membered rings (pyrrole and 1,3-dioxole) and two central six-membered rings (di-hydro-pyridine and benzene). The five-membered 1,3-dioxole ring has an envelope conformation and the central six-membered di-hydro-pyridine ring adopts a twist-boat conformation. The acyl substituent is almost coplanar with the pyrrole ring, whereas the meth-oxy substituent is twisted by 27.93 (16)° relative to the benzene ring. The 2-oxopropan-1-yl substituent is roughly perpendicular to the pyrrole ring. In the crystal, mol-ecules are stacked along the a -axis direction; the stacks are linked by weak C-H⋯O hydrogen bonds into puckered layers lying parallel to (001).