Macrotricyclic host molecules with basket shaped cavities

The syntheses of several macrotricyclic hexalactams (1–3) and of a corresponding hexalactone (4) are described in detail for the first time. The molecules have a basket shaped skeleton and contain a non-collapsible cavity, the size and shape of which is varied by use of spacer groups. Compounds1–3 selectively form crystalline adducts with ethanol as guest; the macrotricyclic hexaester4 does not. Evidence for an interaction of1 with ethanol was obtained by exchange experiments with perdeuteroethanol. Complexation experiments in solution did not show significant host/guest interactions with the guest chosen.