Synthesis of Perhydroindolines by Ring-Opening/Ring-Closing Metathesis

Significance

This constitutes the first report of a tandem stereoselective olefin ring-opening/ring-closing metathesis (RORCM) on 7-azanorbornenes yielding perhydroindoline derivatives in excellent yields. One of the intermediates, having the correct stereochemistry and functionality, was converted into derivatives exhibiting the required backbone of selected perhydroindoline-containing natural products, rostratins B-D (1-3).