Syntheses of (±)-serratine, (±)-lycoposerramine T, and (±)-lycopoclavamine B.

The first total syntheses of (±)-serratine, (±)-lycoposerramine T, and (±)-lycopoclavamine B have been accomplished. The functionalized octahydroindane skeleton of these natural products was constructed by an efficient Diels-Alder reaction of an α-alkynylcyclopentenone and the stereoselective introduction of a tertiary hydroxyl group. Two of these natural products were divergently synthesized from the same synthetic intermediate at a later stage.