Synthesis of a simplified analogue of eleutherobin via a Claisen rearrangement and ring closing metathesis strategy.

The enantioselective synthesis of a simplified eleutherobin analogue by ring closing metathesis (RCM) of the 2,9-divinyl-substituted tetrahydro-oxonin is described; the analogue and an advanced intermediate revealed microtubule stabilising properties in the micromolar range.